Hydrochloric Acid → 2-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-benzoic acid

HRID 925259노트

반응식

HRID 925259 반응식
[SH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Br[CH2:12][CH2:13][C:14]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)([F:16])[F:15].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O.O>[F:16][C:14]([F:15])([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH2:13][CH2:12][S:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 54432-Mercaptobenzoic AcidHCID 11430Potassium CarbonateHCID 671338221-(3-Bromo-1,1-difluoropropyl)-4-fluorobenzene

생성물 1

HCID 867201602-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-benzoic acid수율 37%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

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온도
70 °C

실험 절차

To a solution of 2-mercapto-benzoic acid (0.10 g, 0.65 mmol) in acetone (30 ml) are added 1-(3-bromo-1,1-difluoro-propyl)-4-fluoro-benzene (0.16 g, 0.65 mmol) and potassium carbonate (0.27 g, 1.95 mmol) at RT. The reaction mixture is stirred at 70° C. for 2.5 h. The reaction mixture is diluted with water (20 ml), acidified with 2M hydrochloric acid and the aqueous layer is extracted with EtOAc (3×20 ml). The combined organic layers are washed with water (15 ml), brine (15 ml), dried over sodium sulfate and evaporated to dryness. The crude product is purified by column chromatography (silica gel, 80% EtOAc/hexane) to yield 2-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-benzoic acid (0.08 g, 0.24 mmol, 37%).

후처리

  1. extractionthe aqueous layer is extracted with EtOAc (3×20 ml)
  2. washThe combined organic layers are washed with water (15 ml), brine (15 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude product is purified by column chromatography (silica gel, 80% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-9a05a69ddfdc49daaf341e42d7076f62
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284286B2

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