4'-Bromophenyl Triptycene-2,5-diol

T-Br-PH

M.p. 118.0–119.6 °C

1H-NMR (400 MHz, DMSO-d6): δ = 9.09 (s, 1H), 8.40 (s, 1H), 8.41 (s, 1H), 7.52 (dd, J = 8.4 Hz and 2 Hz,

2H), 7.40 (dd, J = 8.4 Hz and 2 Hz, 4H), 7.32 (dd, J = 8.4 Hz and 2.8 Hz, 2H), 6.97 (dd, J = 8.4 Hz and

2 Hz, 4H). 6.36 (s, 1H), 5.99 (s, 1H), 5.82 (s, 1H).

13C-NMR (100 MHz, DMSO-d6): 146.11, 145.96, 141.72, 138.67, 135.08, 132.29, 131.72, 127.03,

125.28, 125.19, 124.21, 124.03, 120.18, 114.41, 60.20, 47.40, 47.09, 21.21 and 14.55.

MS: m/z (ES), 440.2 [(M−1)−].

Elemental analysis: Calculated for C26H17BrO2 (441.31): C, 70.76%; H, 3.88%; O, 7.25%. Found: C,

70.62%; H, 3.76%; O, 7.17%.

Molbank 2013, 2013(1), M796; doi:10.3390/M796

Short Note

4'-Bromophenyl Triptycene-2,5-diol

Shimoga D. Ganesh ¹, Karkala V. Pai ^1,*  and Mahadevappa Y. Karidurganavar ²

email............vasantapai@gmail.com.

¹ Department of Industrial Chemistry, School of Chemical Sciences, Jnana Sahyadri, Kuvempu University, Shankaraghatta 577451, Shimoga, Karnataka, India² Department of Chemistry and Center of Excellence in Polymer Science, Karnatak University, Dharwad 580003, India

file:///C:/Users/Inspiron/Downloads/molbank-2013-M796%20(1).pdf

Diels Alder reaction of 4-bromophenylquinone (Br-PQ) with anthracene, followed by reduction affords the desired 4'-bromophenyl triptycene-2,5-diol (T-Br-PH). The described synthesis represents a simple and efficient method for the construction of a triptycene ring with a bromophenyl pendant. The intermediate and the final compound (T-Br-PH) have been characterized by elemental analysis, NMR, and LCMS techniques.

4-Bromophenylquinone 

see............file:///C:/Users/Inspiron/Downloads/molbank-2013-M796-s001.pdf

Br-PQ

1H-NMR (400 MHz, DMSO-d6): δ = 7.63 (d, J = 8 Hz, 2H), 7.46 (d, J = 8 Hz, 2H), 6.95 (d, J = 7.2 Hz,

1H), 6.90 (d, J = 10 Hz, 1H), 6.68 (s, 1H).

13C-NMR (100 MHz, DMSO-d6): 150.65, 147.15, 138.44, 131.53, 131.26, 127.21, 120.15, 117.45,

116.61, 115.97.

LCMS: m/z (ES), 262.1 [(M−1)−].

Elemental analysis: Calculated for C12H7BrO2 (263.08): C, 54.78%; H, 2.68%; O, 12.16%. Found: C,

54.52%; H, 2.48%; O, 12.02%.

http://www.kuvempu.ac.in/

Kuvempu University

Kuvempu University, Shankaraghatta 577451, Shimoga, Karnataka, India

Kuvempu University, Shankaraghatta 577451, Shimoga, Karnataka, India

http://www.kuvempuuniversitydde.org/index1.html





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