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

HRID 445114

반응식

HRID 445114 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
130 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-41a8d61ec7344509a0cbc969aa69eb85
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476287B2

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