Boron tribromide → HCID 10171939、化合物

HRID 1835975ノート

反応式

HRID 1835975 の反応式
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

参加物

5

反応物 2

HCID 25134Boron tribromideHCID 10192985HCID 10192985、化合物

生成物 1

HCID 10171939HCID 10171939、化合物収率 88.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 18522661Acetone cardice溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-6bce139f381c44dfa93a278d547cc1a8
出典データセット
uspto-grants-2004_08
特許番号
US06774248B2

反応ノート

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