Pyridine → 2-chloro-N-(3,4-difluorophenyl)acetamide

HRID 333035Notes

Reaction equation

HRID 333035 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].N1C=CC=CC=1.[Cl:16][CH2:17][C:18](Cl)=[O:19]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:18](=[O:19])[CH2:17][Cl:16])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 774693,4-Difluoroaniline

Product 1

HCID 7358532-chloro-N-(3,4-difluorophenyl)acetamideYield 418.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The method of Cervena et al.3 was followed. To a stirred solution of 3,4-difluoroaniline (10 mmol) in toluene (5 mL) and pyridine (10 mmol) maintained at 5-10 deg C was added chloroacetyl chloride (10 mmol) in toluene (5 mL) dropwise. The mixture was allowed to stand overnight at room temperature. The organic layer was then separated and the residue was mixed with water (60 mL). The separated solid product was recrystallized from toluene to give N-(3,4-difluorophenyl) chloroacetamide (8.6 g, 84.3% yield). 1HNMR (300 MHz, CDCl3) δ 8.24 (s, 1H, NH), 7.63 (td, J=8.1 Hz, 1H, Ar—H), 7.16-7.12 (m, 2H, Ar—H), 4.19 (s, 2H, COCH2Cl).

Workup

  1. customThe organic layer was then separated
  2. additionthe residue was mixed with water (60 mL)
  3. customThe separated solid product was recrystallized from toluene

Sources & evidence

ORD record
ord-1b329bdf5dcf4057a813a084da4a4e58
Source dataset
uspto-grants-2014_11
Patent number
US08877946B2

Reaction notes

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