Water → 1-Bromo-4-(isocyanomethyl)-2-methylbenzene

HRID 1505268ノート

反応式

HRID 1505268 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][NH:7][CH:8]=O)=[CH:4][C:3]=1[CH3:12].P(Cl)(Cl)(Cl)=O.O.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][N+:7]#[C-:8])=[CH:4][C:3]=1[CH3:12]

参加物

7

反応物 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 58497978N-(4-bromo-3-methyl-benzyl)-formamide

生成物 1

HCID 584979501-Bromo-4-(isocyanomethyl)-2-methylbenzene収率 114.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-(4-bromo-3-methyl-benzyl)-formamide (Example 10.2) (4.3 g) in dichloromethane (70 ml) was added a solution of phosphorus oxychloride (2.8 g) in dichloromethane (15 ml) at 0-5° C. The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was poured onto a mixture of ice and water (400 ml), and sodium hydrogen carbonate (saturated) (100 ml) and ethyl acetate (250 ml) were added. The phases were separated and the organic phase was washed with brine, dried over sodium sulfate and concentrated to give 1-bromo-4-isocyanomethyl-2-methyl-benzene (4.52 g) as a brown oil. 1H-NMR (400 MHz, CDCl3): 7.54 (m, 1H), 7.22 (s, 1H), 7.03 (m, 1H), 4.57 (s, 2H), 2.42 (s, 3H) ppm.

後処理

  1. additionwere added
  2. customThe phases were separated
  3. washthe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-50efad115de944229eed5ba41d0e2112
出典データセット
uspto-grants-2015_12
特許番号
US09216973B2

反応ノート

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