Boron tribromide → HCID 10171939, 화합물

HRID 1835975노트

반응식

HRID 1835975 반응식
C[O:2][C:3]1[CH:4]=[C:5]([CH2:20]O)[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1.B(Br)(Br)[Br:23]>ClCCl.C(=O)=O.CC(C)=O>[Br:23][CH2:20][C:5]1[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=[C:3]([OH:2])[CH:4]=1

참가 물질

5

반응물 2

HCID 25134Boron tribromideHCID 10192985HCID 10192985, 화합물

생성물 1

HCID 10171939HCID 10171939, 화합물수율 88.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 18522661Acetone cardice용매

실험 절차

Benzyl Alcohol 3 (0.500 g, 1.759 mmole) was dissolved in dichloromethane (50 mL) and cooled to −78° C. in dry ice/acetone bath. To this solution, boron tribromide (1.0 M in dichloromethane), (7.04 mL, 7.05 mmole) was added drop wise over 15 minutes. After 30 minutes, the dark orange solution was allowed to come to room temperature and reacted for an additional 4 hours. The solution was concentrated and added to saturated sodium bicarbonate and extracted with ethyl acetate. Organic layers were combined and washed with water, brine, and dried over magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 7:3) to afford 0.495 g (88%) of benzyl bromide 4 as a white solid: Mp=337-339° C.; 1H NMR (DMSO-d6) δ 7.90 (s, 2 H),), 7.74 (d, 2 H, J=8.8 Hz), 7.06 (s, 1 H), 6.89 (d, 2 H, J=8.7 Hz), 6.86 (d, 1 H, J=2.5 Hz), 6.77 (d, 1 H, J=2.2 Hz); MS 317/319 (M+H)+.

후처리

  1. customto come to room temperature
  2. customreacted for an additional 4 hours
  3. concentrationThe solution was concentrated
  4. additionadded to saturated sodium bicarbonate
  5. extractionextracted with ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe organic phases were concentrated
  9. customchromatographed with silica gel (hexanes:ethyl acetate, 7:3)

출처 및 근거

ORD 기록
ord-6bce139f381c44dfa93a278d547cc1a8
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774248B2

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