Trifluoroacetic acid → 4-(4-Amino-phenoxy)-N-(4-bromo-phenyl)-3-nitro-benzamide

HRID 605136

Reaction equation

HRID 605136 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=3)=[CH:17][C:16]=2[N+:31]([O-:33])=[O:32])=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=3)=[O:30])=[CH:17][C:16]=2[N+:31]([O-:33])=[O:32])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67040702{4-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenoxy]phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 670405064-(4-Amino-phenoxy)-N-(4-bromo-phenyl)-3-nitro-benzamideYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Example 10B (250 mg, 0.4732 mmol) in methylene chloride (5 mL) was treated with trifluoroacetic acid (5 mL) at room temperature for 30 minutes. The solvents were removed by rotary evaporation under vacuum, and the residue taken up in ethyl acetate (100 mL) and washed with saturated aqueous sodium hydrogen carbonate (2×50 mL), water (50 mL), and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the title compound as a light orange solid (197 mg, 97%).

Workup

  1. customThe solvents were removed by rotary evaporation under vacuum
  2. washwashed with saturated aqueous sodium hydrogen carbonate (2×50 mL), water (50 mL), and brine (50 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ab2b9c3289ac4e2fa2c278a73a4f920c
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Linked notes

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