Thionyl Chloride → 3-(Chloromethyl)-4,5-difluorobenzenamine

HRID 2277753Notes

Reaction equation

HRID 2277753 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([F:10])=[C:6]([CH2:8]O)[CH:7]=1.S(Cl)([Cl:14])=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN1C(=O)CCC1>[Cl:14][CH2:8][C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([F:11])[C:5]=1[F:10])[NH2:1]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 72183161(5-Amino-2,3-difluorophenyl)methanol

Product 1

HCID 892397563-(Chloromethyl)-4,5-difluorobenzenamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirring solution of (5-amino-2,3-difluorophenyl)methanol (4.13 g; 25.9 mmol) in DCM (78 mL) and NMP (11 mL) at RT was added dropwise thionylchloride (4.7 mL; 64.9 mmol). The mixture was allowed to react at RT overnight. Then, the mixture was poured into aqueous sodium bicarbonate solution/saturated aqueous sodium chloride solution/ice. The batch was stirred for 2 hours before it was extracted with ethyl acetate (2×). The combined organic phases were filtered using a Whatman filter and concentrated to give crude 3-(chloromethyl)-4,5-difluoroaniline.

Workup

  1. customto react at RT overnight
  2. extractionwas extracted with ethyl acetate (2×)
  3. filtrationThe combined organic phases were filtered
  4. filtrationfilter
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-07b9b936bb7241dfaaade42ee130eeb1
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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