4-Bromoaniline → HCID 22346912, compound

HRID 897885Notes

Reaction equation

HRID 897885 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Br:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.C(N(CC)C(C)C)(C)C>ClCCl>[Br:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:2]=2[F:1])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 81531DiisopropylethylamineHCID 1455802-Fluoro-4-(trifluoromethyl)benzoyl chloride

Product 1

HCID 22346912HCID 22346912, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-fluoro-4-(trifluoromethyl)benzoyl chloride (5.05 g, 0.0223 mol) and 4-bromoaniline (3.83 g, 0.0223 mol) in anhydrous dichloromethane (150 mL) was cooled to 0° C. and N,N-diisopropylethylamine (4.26 mL, 0.0245 mol) was added under nitrogen atmosphere dropwise. The resulting mixture was stirred at ambient temperature for 24 hours, concentrated and the residue was partitioned between ethyl acetate (120 mL) and water (100 mL). The organic phase was washed with brine, dried with magnesium sulfate and concentrated. The residue was suspended in cold n-heptane (50 mL) and the precipitate was collected by filtration and dried to yield N1-(4-bromophenyl)-2-fluoro-4-(trifluoromethyl)benzamide (7.1 g, 0.0196 mol) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 10.74 (s, 1H), 7.90 (m, 2H), 7.74 (d, 1H), 7.68 (d, 2H), 7.56 (d, 2H).

Workup

  1. concentrationconcentrated
  2. customthe residue was partitioned between ethyl acetate (120 mL) and water (100 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. filtrationthe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-2b9b5d8870e54862b9e7c31952d84f77
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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