Methanol → Methyl 2-(3,5-difluorophenyl)-2-hydroxyacetate

HRID 1037754Notes

Reaction equation

HRID 1037754 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:13])[C:10]([OH:12])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.B(O)(O)O.[CH3:18]O>>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:13])[C:10]([O:12][CH3:18])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 7628Boric AcidHCID 5886483,5-Difluoromandelic acid

Product 1

HCID 22312159Methyl 2-(3,5-difluorophenyl)-2-hydroxyacetate

Procedure

25.0 g of 3,5-difluorophenylhydroxyacetic acid (D2) are dissolved in 325 ml of methanol. 3.9 g of boric acid are subsequently added, and the reaction mixture is stirred at room temperature for 18 hours. The resultant solution is then evaporated to dryness. The residue is extracted using 100 ml of ethyl acetate and 100 ml of water. The aqueous phase is subsequently extracted twice with 50 ml of ethyl acetate each time. The combined organic phases are dried over sodium sulfate and filtered. The filtrate is evaporated to dryness in vacuo, giving 25.5 g of the title compound as crude product. Recrystallisation from 17 ml of ethyl acetate and 170 ml of cyclohexane give 23.5 g of the pure compound C2 having a melting point of 61.8° C. (MS 201.9 (M+)).

Workup

  1. customThe resultant solution is then evaporated to dryness
  2. extractionThe residue is extracted
  3. extractionThe aqueous phase is subsequently extracted twice with 50 ml of ethyl acetate each time
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate is evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5f9aac7c55a047b18bbdcba136ebae20
Source dataset
uspto-grants-2013_10
Patent number
US08546613B2

Reaction notes

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