Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

HRID 73136

반응식

HRID 73136 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][Si:14]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 701194-Bromobenzyl alcohol

생성물 1

HCID 108595834-Bromobenzyloxy-tert-butyldimethylsilane수율 89.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Bromobenzyl alcohol (50.00 g, 267.3 mmol), tert.-butyldimethylsilyl chloride (52.38 g, 347.5 mmol), and imidazole (23.66 g, 347.5 mmol) were dissolved in anhydrous DMF (300 mL). This solution was allowed to stir at room temperature overnight and then poured into ice-water (600 mL). The organic layer was separated off and washed with saturated aqueous sodium bicarbonate (2×200 mL) and water (2×200 mL). We obtained colorless oil (71.9 g, 88%): 1H NMR (CDCl3): δ 0.10 (s, (CH3)2Si), 0.94 (s, (CH3)3C), 4.7 (s, CH2O), 7.20 (d, J=7.8 Hz, C6H4), 7.45 (d, J=7.8 Hz, C6H4); 13C NMR (CDCl3): δ.

후처리

  1. customThe organic layer was separated off
  2. washwashed with saturated aqueous sodium bicarbonate (2×200 mL) and water (2×200 mL)

출처 및 근거

ORD 기록
ord-ec9cded50846470ea94b58b2ff5bc129
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829033B2

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