Hypofluorous acid, trifluoromethyl ester → 4-Chloro-α-fluorobenzeneacetic acid

HRID 2058296Notes

Reaction equation

HRID 2058296 reaction equation
C[Si](C)(C)[O:3][C:4]([O:13][Si](C)(C)C)=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.[F:20]OC(F)(F)F>C(Cl)(Cl)(Cl)F>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]([F:20])[C:4]([OH:13])=[O:3])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 78989Hypofluorous acid, trifluoromethyl esterHCID 11255491HCID 11255491, compound

Product 1

HCID 126021134-Chloro-α-fluorobenzeneacetic acidYield 53%

Reagents, catalysts & solvents 1

HCID 6389TrichlorofluoromethaneSolvent

Procedure

A solution of 29.92 g (0.095 mol) of the aforesaid β,β-bis(trimethylsiloxy)p-chlorostyrene in 300 ml of CFCl3 was cooled to -70° C. and 9.88 g (0.095 mol) of trifluoromethyl hypofluorite were passed into the solution over a period of 2 hours. The mixture was allowed to warm to room temperature and evaporated to dryness under reduced pressure. The resultant white solid residue was stirred with 10 ml of water for approximately 10 minutes. The solids were recrystallized from 1 l of hexane to give 9.38 g (53% yield) of p-chlorophenylfluoroacetic acid as shiny white crystals, mp 66°-68° C.; 1H NMR (CDCl3) δ5.75 (d, J≅47 Hz, 1H), δ7.35 ppm (s, 4H), δ10.95 (s, 1H); 19F NMR (CDCl3) δ-182.60 (d, J≅47 Hz).

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe solids were recrystallized from 1 l of hexane

Sources & evidence

ORD record
ord-4dfc864fa4bc41a691de8ec14d669d55
Source dataset
uspto-grants-1980_07
Patent number
US04215044

Reaction notes

Loading…