Thionyl Chloride → (4'-Chloro-3'-fluoro-4-methylbiphenyl-3-yl)acetyl chloride

HRID 922114Notes

Reaction equation

HRID 922114 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH2:15][C:16](O)=[O:17])[CH:9]=2)=[CH:4][C:3]=1[F:19].S(Cl)([Cl:22])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH2:15][C:16]([Cl:22])=[O:17])[CH:9]=2)=[CH:4][C:3]=1[F:19]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 67375533(4'-Chloro-3'-fluoro-4-methylbiphenyl-3-yl)acetic acid

Product 1

HCID 86676714(4'-Chloro-3'-fluoro-4-methylbiphenyl-3-yl)acetyl chloride

Conditions

Temperature
80 °C

Procedure

10.00 g (35.88 mmol) of (4′-chloro-3′-fluoro-4-methylbiphenyl-3-yl)acetic acid (Example 1A) were dissolved in 24.33 g (204.51 mmol) of thionyl chloride. The reaction mixture was stirred at 80° C. for one hour and then concentrated under reduced pressure. Drying under fine vacuum gave 10.54 g (99% of theory) of the title compound as a brownish oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customDrying under fine vacuum

Sources & evidence

ORD record
ord-31d95c05899e4440813f3acae9735a28
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

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