Chloroacetyl chloride → HCID 89405839, compound

HRID 1396334Notes

Reaction equation

HRID 1396334 reaction equation
[Cl:1][C:2]1[C:3]([F:13])=[C:4]([C:6]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:8]=1)[NH2:5].C([O-])([O-])=O.[K+].[K+].[Cl:20][CH2:21][C:22](Cl)=[O:23]>C1COCC1>[Cl:20][CH2:21][C:22]([NH:5][C:4]1[C:6]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:8]=[C:2]([Cl:1])[C:3]=1[F:13])=[O:23]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 57361729HCID 57361729, compound

Product 1

HCID 89405839HCID 89405839, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-chloro-2-fluoro-6-(trifluoromethyl)aniline (250 mg, 1.136 mmol) in THF (2 mL) was added K2CO3 (235 mg, 1.703 mmol). The mixture was cooled to 0° C. and added 2-chloroacetyl chloride (0.099 mL, 1.249 mmol). The ice-water bath was removed and the reaction was allowed to warm to rt. After stirred at rt overnight, The reaction mixture was diluted with ether and water. The organic ether layer was separated and washed with brine, dried over MgSO4, filtered and concentrated to yield a crude white solid product, which was purified by silica gel chromatography to yield desired product (280 mg, 85%) as a white solid. 1H NMR (500 MHz, CDCl3) δ 8.06 (br. s., 1H), 7.55-7.49 (m, 1H), 7.48-7.42 (m, 1H), 4.27 (s, 2H). MS (ESI) m/z: 289.9 (M+H)+.

Workup

  1. customThe ice-water bath was removed
  2. temperatureto warm to rt
  3. additionThe reaction mixture was diluted with ether and water
  4. customThe organic ether layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a crude white solid product, which
  10. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-4284309bd9604fb7b0a6e5ff94f96ffc
Source dataset
uspto-grants-2014_12
Patent number
US08901115B2

Reaction notes

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