Triethylamine → 3-bromo-4-fluoro-N-(2-fluoro-3-(trifluoromethyl)phenyl)benzamide

HRID 1042730Notes

Reaction equation

HRID 1042730 reaction equation
[F:1][C:2]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[F:23])[C:17](Cl)=[O:18].C(N(CC)CC)C>ClCCl>[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[F:23])[C:17]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[C:8]([C:9]([F:10])([F:11])[F:12])[C:2]=1[F:1])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 695983-Bromo-4-fluorobenzoyl chlorideHCID 1455693-Amino-2-fluorobenzotrifluoride

Product 1

HCID 594279983-bromo-4-fluoro-N-(2-fluoro-3-(trifluoromethyl)phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Fluoro-3-(trifluromethyl)aniline (0.515 g, 0.37 mL, 2.88 mmol) was added to a solution of 3-bromo-4-fluorobenzoyl chloride (0.650 g, 2.74 mmol) in dichloromethane (5 ml), and the mixture stirred at room temperature for 30 min. Triethylamine (0.360 g, 0.50 ml, 3.56 mmol) was added and the solution stirred at room temperature for 1 h. The reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with water, brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a light yellow solid. Trituration with dichloromethane and filtering afforded 3-bromo-4-fluoro-N-(2-fluoro-3-(trifluoromethyl)phenyl)benzamide as a white solid. MS (M−H+) 377.9; Calculated for C14H7BrF5NO: 379.

Workup

  1. stirringthe solution stirred at room temperature for 1 h
  2. customThe reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  3. customThe aqueous phase was separated
  4. extractionextracted with dichloromethane
  5. washThe combined organic phases were washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a light yellow solid
  10. filtrationTrituration with dichloromethane and filtering

Sources & evidence

ORD record
ord-65ca380cbc5240f69c22d949f24214c8
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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