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

HRID 1871489

反応式

HRID 1871489 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 227070173-(o-Bromobenzyloxy)4-methoxybenzonitrile収率 71.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-725f9954f649420c8fe12b745486b187
出典データセット
uspto-grants-2000_08
特許番号
US06103738

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