Phosphorus oxybromide → HCID 85866305, compound

HRID 1365094Notes

Reaction equation

HRID 1365094 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](O)=O)([CH3:3])[CH3:2].P(Br)(Br)([Br:22])=O>>[Br:22][C:13]1[C:12]2[C:11]([N:10]=[C:5]3[C:6]=1[CH:7]=[CH:8][CH:9]=[C:4]3[CH:1]([CH3:3])[CH3:2])=[CH:19][CH:18]=[CH:17][CH:16]=2

Participants

3

Reactant 2

HCID 24613Phosphorus oxybromideHCID 10890491N-(2-Isopropylphenyl)anthranilic acid

Product 1

HCID 85866305HCID 85866305, compoundYield 102.5%

Conditions

Temperature
120 °C

Procedure

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.

Workup

  1. customExcess phosphorus oxybromide was removed by distillation
  2. additionthe residual solution was poured into a 1:1 mixture of aqueous ammonium hydroxide
  3. customThe CH2Cl2 solution was separated
  4. customdried
  5. filtrationfiltered
  6. customthe combined organic layers was dried in vacuum

Sources & evidence

ORD record
ord-4f2368e9129540deb9cc8732595bf921
Source dataset
uspto-grants-2011_02
Patent number
US07888509B2

Reaction notes

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