Thionyl Chloride → 4-(Benzyloxy)-2-fluorobenzoyl chloride

HRID 2280405Notes

Reaction equation

HRID 2280405 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[C:11]([F:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([Cl:21])=[O:14])=[C:11]([F:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 223145024-(Benzyloxy)-2-fluorobenzoic acid

Product 1

HCID 540579464-(Benzyloxy)-2-fluorobenzoyl chloride

Procedure

4-Benzyloxy-2-fluoro-benzoic acid (2 g, 8.12 mmol) was suspended in thionyl chloride (5.9 mL) and heated to reflux for 30 minutes. The reaction mixture was then concentrated under reduced pressure, and the resulting residue was dissolved in toluene and re-concentrated twice to remove residual thionyl chloride. This procedure provided the title compound in crude form, which was used in the next reaction without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 minutes
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. dissolutionthe resulting residue was dissolved in toluene
  5. concentrationre-concentrated twice
  6. customto remove residual thionyl chloride

Sources & evidence

ORD record
ord-40d5dfb15c224c75bd19038343984b33
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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