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

HRID 925259ノート

反応式

HRID 925259 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-9a05a69ddfdc49daaf341e42d7076f62
出典データセット
uspto-grants-2016_03
特許番号
US09284286B2

反応ノート

読み込み中…