Methanol → HCID 66608247, compound

HRID 2174629Notes

Reaction equation

HRID 2174629 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][C:11]([OH:13])=[O:12].S(Cl)(Cl)=O.O.[CH3:19]O>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][C:11]([O:13][CH3:19])=[O:12]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24386Thionyl ChlorideHCID 27779512-(2,4,6-Trifluorophenyl)acetic acid

Product 1

HCID 66608247HCID 66608247, compound

Procedure

A solution of 2,4,6-trifluorobenzeneacetic acid (5.00 g, 26.3 mmol) in methanol (25 mL) was stirred at ambient temperature, and thionyl chloride (6 mL, ˜3 eq.) was added dropwise, causing the temperature of the reaction mixture to reach 60° C. The reaction mixture was allowed to cool to ambient temperature and was stirred for 3 h. Water (25 mL) was added with ice cooling. The mixture was extracted with ethyl acetate (2×100 mL). The combined organic phases were washed with water (2×), with saturated aqueous sodium bicarbonate solution and with brine, and dried over MgSO4. Concentration provided the title product as a clear oil (5.38 g).

Workup

  1. customto reach 60° C
  2. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  3. washThe combined organic phases were washed with water (2×), with saturated aqueous sodium bicarbonate solution and with brine
  4. dry with materialdried over MgSO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-77705a0e77e642ff9c3661f1ddef76b0
Source dataset
uspto-grants-2015_06
Patent number
US09062005B2

Reaction notes

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