3-(Trifluoromethyl)aniline → 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide

HRID 1991229Notes

Reaction equation

HRID 1991229 reaction equation
BrCC(Br)=O.[Br:6][CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1)=[O:9].FC(F)(F)C1C=C(C=CC=1)N.C(N(CC)CC)C>C1COCC1>[Br:6][CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=1)=[O:9]

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 8471TriethylamineHCID 86609658HCID 86609658, compound

Product 1

HCID 23171522-bromo-N-[3-(trifluoromethyl)phenyl]acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Part A: Synthesis of 2-bromo-N-(3-trifluoromethyl-phenyl)-acetamide Bromoacetyl bromide (1.41 g, 7 mmol) was added under stirring to a solution of 3-trifluoromethyl-aniline (0.77 g, 4.8 mmol) and triethylamine (0.83 mL, 8.2 mmol) in THF (60 mL) at 0° C. The reaction was stirred for 3 h at 0° C. and the solvent was evaporated. The crude product was purified by flash chromatography (Silica, heptane/ethyl acetate 1:1) to afford 2-bromo-N-(3-trifluoromethyl-phenyl)-acetamide (1.35 g, 100%). Mass spectrum (ESI) m/z: 280.0, 282.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.93 (s, 2H), 7.31 (d, J=8.1 Hz, 1H), 7.44 (t, J=7.8 Hz, 1H), 7.63 (d, J=8.1 Hz, 1H), 7.93 (s, 1H), 10.57 (s, 1H).

Workup

  1. additionwas added
  2. customthe solvent was evaporated
  3. customThe crude product was purified by flash chromatography (Silica, heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-39bbe8465ce64166ae0ff01805dd6cd7
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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