Water → HCID 67377647, compound

HRID 217463Notes

Reaction equation

HRID 217463 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:15]O)[CH:5]=[CH:6][C:7]=1[O:8][C@@H:9]([CH3:14])[C:10]([F:13])([F:12])[F:11].O=S(Cl)[Cl:19].O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:15][Cl:19])[CH:5]=[CH:6][C:7]=1[O:8][C@@H:9]([CH3:14])[C:10]([F:13])([F:12])[F:11]

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 67363540HCID 67363540, compound

Product 1

HCID 67377647HCID 67377647, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {3-chloro-4-[(1S)-2,2,2-trifluoro-1-methylethoxy]phenyl}methanol (284 mg) and SOCl2 (179 μL) in DCM (7 mL) was stirred at room temperature for 2 hours. The reaction liquid was poured into water, followed by extraction with chloroform. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure to obtain 2-chloro-4-(chloromethyl)-1-[(1S)-2,2,2-trifluoro-1-methylethoxy]benzene (285 mg) as a colorless liquid.

Workup

  1. customThe reaction liquid
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-135539d065034defaa2e77c9d45453fa
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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