Sodium hydride → 3-(o-Bromobenzyloxy)4-methoxybenzonitrile

HRID 1871489

반응식

HRID 1871489 반응식
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[H-].[Na+].F[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:16]#[N:17]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:5][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:16]#[N:17]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 728502-Bromobenzyl alcoholHCID 27745483-Fluoro-4-methoxybenzonitrile

생성물 1

HCID 227070173-(o-Bromobenzyloxy)4-methoxybenzonitrile수율 71.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a solution of 2-bromobenzyl alcohol (16.50 g, 88.2 mmol) in DMF (100 ml) was added sodium hydride (60% dispersion in mineral oil, 2.94 g, 73.5 mmol) and this was followed by 3-fluoro-4-methoxybenzonitrile (8.88 g, 58.8 mmol) and the resulting mixture was heated to 90° C. for 2 h under N2. After cooling, the mixture was partitioned between ether and H2O, the organic layer washed sequentially with 0.5N HCl and saturated brine and then dried over MgSO4. Trituration with ether/pentane (1/, v/v) afforded the subtitle compound as an off-white solid (13.35 g, 71%). Rf 0.27 (hexane/EtOAc 5/1, v/v). MS m/z 318, 320 (MH+).

후처리

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between ether and H2O
  3. washthe organic layer washed sequentially with 0.5N HCl and saturated brine
  4. dry with materialdried over MgSO4

출처 및 근거

ORD 기록
ord-725f9954f649420c8fe12b745486b187
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06103738

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