2-Bromoaniline → HCID 623433, compound

HRID 1596096Notes

Reaction equation

HRID 1596096 reaction equation
[Br:1][C:2]1[C:3](I)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O-:7])=[O:6].[Na+].[H-].[Na+].[Br:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18]>O1CCCC1.[Cu]>[Br:1][C:2]1[C:3]([NH:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[Br:15])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 119922-BromoanilineHCID 24758Sodium hydride2×HCID 23703752HCID 23703752, compound2×

Product 1

HCID 623433HCID 623433, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 16.0 g (46 mmol) of sodium 3-bromo-2-iodobenzoate [prepared from 15.0 g (46 mmol) of 3-bromo-2-iodobenzoic acid (XX) and 1.1 g (46 mmol) of sodium hydride], 19.5 g (100 mmol) of sodium 2-bromoanilide [prepared from 17.3 g (100 mmol) of 2-bromoaniline (XXI) and 2.4 g (100 mmol) of sodium hydride] and a spatula-tipfull of copper powder in 100 ml of tetrahydrofuran was heated to reflux for 9 h. The solvent was distilled off, the residue extracted with 0.5 M aqueous sodium hydroxide, and the resulting suspension subjected to centrifugation. The centrifugate was acidified with diluted hydrochloric acid, the precipitated solid was filtered off and dried under high vacuum. Fractional sublimation under high vacuum yielded 6.3 g (37% of theory) of 3-bromo-2-(2-bromophenylamino)benzoic acid (XXII) as a yellow powder with a melting point of 181-182° C.

Workup

  1. temperatureto reflux for 9 h
  2. distillationThe solvent was distilled off
  3. extractionthe residue extracted with 0.5 M aqueous sodium hydroxide
  4. filtrationthe precipitated solid was filtered off
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-6cac769a10054e02b8ac0a17f8385168
Source dataset
uspto-grants-2001_09
Patent number
US06290926B1

Reaction notes

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