Acetyl chloride → 4-Bromo-2-fluoro-benzimidic acid ethyl ester hydrochloride

HRID 2044413Notes

Reaction equation

HRID 2044413 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.[C:11]([Cl:14])(=[O:13])[CH3:12]>>[ClH:14].[CH2:11]([O:13][C:6](=[NH:7])[C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][C:4]=1[F:10])[CH3:12]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 7360294-Bromo-2-fluorobenzonitrile

Product 1

HCID 670507354-Bromo-2-fluoro-benzimidic acid ethyl ester hydrochlorideYield 57.5%

Procedure

A suspension of 4-bromo-2-fluorobenzonitrile (25.0 g, 125 mmol) in IMS (88 mL) at 0-5° C. and treated dropwise with acetyl chloride (71 mL, 1 mol) maintaining the temperature below 10° C. The reaction vessel was sealed and the mixture stirred at RT for 18 h before concentrating in vacuo. The resultant residue was triturated in diethyl ether to give 4-Bromo-2-fluoro-benzimidic acid ethyl ester hydrochloride as a white solid (20.3 g, 57%). 1H NMR δ (ppm) (DMSO-d): 7.93-7.88 (1H, m), 7.85-7.76 (1H, m), 7.72-7.64 (1H, m), 4.60 (2H, q, J=7.02 Hz), 1.47-1.38 (3H, m).

Workup

  1. temperaturemaintaining the temperature below 10° C
  2. customThe reaction vessel was sealed
  3. concentrationbefore concentrating in vacuo
  4. customThe resultant residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-7633aa9c21de4031a9514f84071aefc9
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

Loading…