Bromine → 4-Bromo-2-[(trifluoromethyl)sulfanyl]phenol

HRID 638953노트

반응식

HRID 638953 반응식
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]([F:12])([F:11])[F:10].[Br:13]Br>C(Cl)Cl.O>[Br:13][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([S:8][C:9]([F:12])([F:10])[F:11])[CH:4]=1

참가 물질

5

반응물 2

HCID 24408BromineHCID 101765072-[(trifluoromethyl)sulfanyl]phenol

생성물 1

HCID 686856734-Bromo-2-[(trifluoromethyl)sulfanyl]phenol수율 93%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

To a stirred solution of 1-hydroxy-2-trifluoromethylthiobenzene (16 mmol, 1.0 eq.) in CH2Cl2 (40 mL) at −78° C. was added a solution of Br2 (0.83 mL, 16 mmol, 1.0 eq.) in CH2Cl2 (18 mL) slowly. The resulting mixture was stirred at −78° C. for 2 h and then warmed to room temperature overnight. The reaction mixture was diluted with water (300 mL) and extracted with CH2Cl2 (3×150 mL). The combined organic layer was washed with brine (400 mL), dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography using 0-10% EtOAc in hexanes as an eluent to afford 4-bromo-1-hydroxy-2-trifluoromethylthiobenzene in 93% yield as a crystalline solid.

후처리

  1. temperaturewarmed to room temperature overnight
  2. extractionextracted with CH2Cl2 (3×150 mL)
  3. washThe combined organic layer was washed with brine (400 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-ffeb37b852f64469997f16b077af38bf
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691843B2

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