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

HRID 2058296노트

반응식

HRID 2058296 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 126021134-Chloro-α-fluorobenzeneacetic acid수율 53%

시약·촉매·용매 1

HCID 6389Trichlorofluoromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-4dfc864fa4bc41a691de8ec14d669d55
출처 데이터셋
uspto-grants-1980_07
특허 번호
US04215044

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