Hydrochloric Acid → [4-[2-Chloro-4-(trifluoromethyl)phenoxy]phenyl]boronic acid

HRID 445114

反応式

HRID 445114 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1F.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([B:20]([OH:22])[OH:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([B:20]([OH:22])[OH:21])=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 157153Benzene, 2-chloro-1-fluoro-4-(trifluoromethyl)-HCID 27343604-Hydroxyphenylboronic acid

生成物 1

HCID 67972395[4-[2-Chloro-4-(trifluoromethyl)phenoxy]phenyl]boronic acid収率 13.2%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
130 °C

実験手順

A solution of 2-chloro-1-fluoro-4-(trifluoromethyl)benzene (0.95 g), (4-hydroxyphenyl)boronic acid (0.66 g), and potassium carbonate (1.65 g) in DMSO (5.0 mL) was heated with stirring at 130° C. for 20 hours. The resultant reaction mixture was left to be cooled down and was poured into an ice water, and pH of the resultant reaction mixture was adjusted to around 2 with a 10% hydrochloric acid, followed by extracting the reaction mixture with ethyl acetate. From the organic phase, the solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate 100:0 to 50:50) to obtain the subject compound (0.20 g) as a white solid.

後処理

  1. customThe resultant reaction mixture
  2. waitwas left
  3. temperatureto be cooled down
  4. customreaction mixture
  5. extractionby extracting the reaction mixture with ethyl acetate
  6. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
  7. customthe resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate 100:0 to 50:50)

出典と根拠

ORDレコード
ord-41a8d61ec7344509a0cbc969aa69eb85
出典データセット
uspto-grants-2013_07
特許番号
US08476287B2

関連ノート

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