Acetyl chloride → N-(5-Bromo-2-fluorobenzyl)acetamide

HRID 606811Notes

Reaction equation

HRID 606811 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].Cl.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([F:15])=[C:11]([CH:14]=1)[CH2:12][NH2:13].C(N(C(C)C)CC)(C)C>ClCCl.C(OCC)C>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([F:15])=[C:11]([CH:14]=1)[CH2:12][NH:13][C:1](=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 27249035-Bromo-2-fluorobenzylamine hydrochloride

Product 1

HCID 52201827N-(5-Bromo-2-fluorobenzyl)acetamideYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Add acetyl chloride (0.18 mL, 2.49 mmol) to a mixture of 5-bromo-2-fluorobenzylamine hydrochloride (500 mg, 2.08 mmol) in dichloromethane (8 mL) and diisopropylethylamine (0.90 mL, 5.20 mmol) and stir 3 h. Dilute with diethyl ether and separate the layers. Wash the organic layer twice with 1 N hydrochloric acid and once with an aqueous saturated solution of sodium chloride. Dry (sodium sulfate), filter, and concentrate to give the title compound as a white crystalline solid (490 mg, 96%).

Workup

  1. customseparate the layers
  2. washWash the organic layer twice with 1 N hydrochloric acid
  3. dry with materialDry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-61c06d5e1ae049f594f7c62682373030
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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