Boron tribromide → (4E)-3-(4-Chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexen-1-ol

HRID 1634377노트

반응식

HRID 1634377 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:27][CH2:28][O:29]C)/[C:9](/[F:26])=[C:10](\[F:25])/[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8](/[C:9](/[F:26])=[C:10](\[F:25])/[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)[CH2:27][CH2:28][OH:29])=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 25134Boron tribromideHCID 120566491-[(2E)-4-(4-Chlorophenyl)-2,3-difluoro-6-methoxy-2-hexenyl]-3-phenoxybenzene

생성물 1

HCID 59032878(4E)-3-(4-Chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexen-1-ol수율 72.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of 1-[(2E)-4-(4-chlorophenyl)-2,3-difluoro-6-methoxy-2-hexenyl]-3-phenoxybenzene (0.081 g, 0.189 mmol) in methylene chloride at −5° C. under nitrogen was added dropwise boron tribromide (0.5 ml of a 1 M solution in methylene chloride, 0.5 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight at room temperature. The reaction mixture was cooled to −5° C., diluted with methanol (10 ml) and concentrated in vacua. The residue was taken up in methanol (10 ml) and the solution again concentrated. The residue was taken up in methylene chloride (25 ml), washed successively with water, saturated aqueous sodium bicarbonate and water, dried over anhydrous sodium sulfate and concentrated in vacuo to a brown gum. Chromatography of this gum on silica gel afforded the title compound as a tan syrup (0.057 g) which was characterized by 1HNMR, 19FNMR and mass spectral analysis.

후처리

  1. temperatureThe reaction mixture was cooled to −5° C.
  2. concentrationconcentrated in vacua
  3. concentrationthe solution again concentrated
  4. washwashed successively with water, saturated aqueous sodium bicarbonate and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo to a brown gum

출처 및 근거

ORD 기록
ord-af3eb2f1531d4e9090bee3447cce8b4b
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506800B2

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