Water → 6-Hydroxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

HRID 556355ノート

反応式

HRID 556355 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:15]3[CH:16]=[CH:17][C:18]([O:20]C)=[CH:19][C:14]=3[S:13][N:12]=2)=[O:10])=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].B(Br)(Br)Br.O.CCOC(C)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:15]3[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:14]=3[S:13][N:12]=2)=[O:10])=[CH:4][C:3]=1[C:22]([F:24])([F:23])[F:25]

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 669929426-Methoxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

生成物 1

HCID 1363466286-Hydroxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
45 °C

実験手順

A suspension of 252 mg (0.68 mMol) 6-methoxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide in 15 ml CH2Cl2 is cooled in an ice-bath, then 20 ml of a 1 M solution of BBr3 in CH2Cl2 are added. The suspension is stirred for 3 days at 45° C., the resulting solution is cooled, poured into water and EtOAc, the aq. layer is separated off and extracted twice with EtOAc. The organic layers are washed twice with water and sat. NaHCO3, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; acetone/hexane 1:95→2:3) gives the title compound: MS: [M−1]=355; TLC(hexane/acetone 2:1): Rf=0.46.

後処理

  1. temperatureis cooled in an ice-bath
  2. temperaturethe resulting solution is cooled
  3. customthe aq. layer is separated off
  4. extractionextracted twice with EtOAc
  5. washThe organic layers are washed twice with water and sat. NaHCO3
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-dafc320054874d4db0ccd81830b58111
出典データセット
uspto-grants-2011_11
特許番号
US08058276B2

反応ノート

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