Potassium Carbonate → 5-(Chloromethyl)-2-fluoro-N-phenylaniline

HRID 638636Notes

Reaction equation

HRID 638636 reaction equation
P(Cl)(Cl)([Cl:3])=O.[NH:6]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[F:21])[CH2:16]O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>>[NH:6]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[F:21])[CH2:16][Cl:3])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 53906123(3-Anilino-4-fluorophenyl)methanol

Product 1

HCID 202529185-(Chloromethyl)-2-fluoro-N-phenylanilineYield 88.3%

Procedure

Two grams of phosphorus oxychloride was added to 470 mg of 3-anilino-4-fluorobenzyl alcohol with ice-cooling, and the mixture was stirred for 1 hour and then for further 12 hours at 15° C. Thereafter, the reaction solution was poured into a 10% aqueous potassium carbonate solution and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous sodium chloride liquor and dried over anhydrous magnesium sulfate. The solvent was then removed by evaporation to obtain 450 mg of 3-anilino-4-fluorobenzyl chloride.

Workup

  1. temperaturecooling
  2. waitfor further 12 hours at 15° C
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous sodium chloride liquor
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then removed by evaporation

Sources & evidence

ORD record
ord-7d8dbe05ac4e46788507df0125ff600f
Source dataset
uspto-grants-1985_12
Patent number
US04562213

Reaction notes

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