Phosphorus oxybromide → HCID 85866305, compound

Participants

Reaction Conditions

Reaction Steps

2-(2′-Isopropylphenylamino)benzoic acid 8 (1.0 g, 3.9 mmol) was suspended in 11.0 g (38 mmol) of phosphorus oxybromide, and the mixture was heated to 120° C. for 2 hours. Excess phosphorus oxybromide was removed by distillation and the residual solution was poured into a 1:1 mixture of aqueous ammonium hydroxide:CH2Cl2. The CH2Cl2 solution was separated, dried, filtered, and the combined organic layers was dried in vacuum to give 10 (1.2 g, 79%) as yellow powder. 1H-NMR δ=1.45 (d, J=6.9 Hz, 6H), 4.56 (sept, J=6.9 Hz, 1H), 7.56-7.70 (m, 3H), 7.78 (ddd, J=1.5 Hz, J=6.6 Hz, J=6.6 Hz, 1H), 8.24 (d, J=8.4 Hz, 1H), 8.29 (dd, J=1.5 Hz, J=8.5 Hz, 1H), 8.41 (d, J=8.8 Hz, 1H). 13C-NMR δ=24.00, 28.21, 125.20, 125.62, 125.86, 126.49, 127.38, 127.64, 129.90, 130.58, 130.83, 135.69, 147.44, 148.01, 148.14. Anal. calcd. for C16H14NBr: C, 64.02; H, 4.70; N, 4.67. Found: C, 64.23; H, 4.78; N, 4.59.

Provenance & Evidence