Acetic Anhydride → N-(3-bromo-4-fluorobenzyl)acetamide

HRID 661875Notes

Reaction equation

HRID 661875 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH2:10][NH2:11])[CH:6]=[CH:7][C:8]=1[F:9].[C:12](OC(=O)C)(=[O:14])[CH3:13]>N1C=CC=CC=1>[Br:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[F:9])[CH2:10][NH:11][C:12](=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 27249011-(3-Bromo-4-fluorophenyl)methanamine hydrochloride

Product 1

HCID 59374995N-(3-bromo-4-fluorobenzyl)acetamideYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (3-bromo-4-fluorophenyl)methanamine hydrochloric acid salt (500 mg, 2.079 mmol) in pyridine (6 mL) was stirred on ice and treated with acetic anhydride (0.235 mL, 2.495 mmol). The resulting solution was stirred at rt for 17 h, then was concentrated. The residue was stirred in 1 M hydrochloric acid, forming a precipitate which was collected by filtration, rinsed with water and dried to provide N-(3-bromo-4-fluorobenzyl)acetamide as a white solid (435 mg, 85%). 1H NMR (400 MHz, chloroform-d) δ 7.47 (dd, J=6.6, 2.2 Hz, 1H) 7.20 (ddd, J=8.6, 4.6, 2.2 Hz, 1H) 7.07 (t, J=8.3 Hz, 1H) 5.84 (br. s., 1H) 4.38 (d, J=5.9 Hz, 2H) 2.04 (s, 3H). Mass spectrum m/z 246, 248 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. stirringThe residue was stirred in 1 M hydrochloric acid
  3. customforming a precipitate which
  4. filtrationwas collected by filtration
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-1180def49ae14738951346f70ef02c58
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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