Thionyl Chloride → HCID 67087247, compound

HRID 604195Notes

Reaction equation

HRID 604195 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=1[CH2:20]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=1[CH2:20][Cl:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67087250HCID 67087250, compound

Product 1

HCID 67087247HCID 67087247, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Benzyloxy-5-trifluoromethoxy-phenyl)-methanol (510 mg) is dissolved in methylene chloride (5 ml) and thereto is added thionyl chloride (198 μl) and the mixture is stirred at room temperature for 2 hours. The reaction solution is concentrated under reduced pressure and the residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→4:1) to give 1-benzyloxy-2-chloromethyl-4-trifluoromethoxy-benzene (360 mg). 1H-NMR (CDCl3): δ 4.67 (2H, s), 5.14 (2H, s), 6.91 (1H, d), 7.10-7.45 (7H, m)

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. customthe residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→4:1)

Sources & evidence

ORD record
ord-c8038fa8abb04248800f5583303b7f58
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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