Benzyl Bromide → HCID 264185、化合物

HRID 2373131ノート

反応式

HRID 2373131 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>CO>[CH2:12]([S:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 80597m-BromobenzenethiolHCID 10942334Sodium Methoxide

生成物 1

HCID 264185HCID 264185、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

3-bromobenzenethiol (5 g, 26.44 mmol) was added to a solution of sodium methoxide (1.43 g, 26.48 mmol) in 20 ml of anhydrous methanol. The mixture was stirred for 30 min at room temperature and a solution of benzyl bromide (4.53 g, 26.48 mmol) in 20 ml anhydrous methanol was then added. The reaction mixture was stirred overnight at room temperature, poured into 2M o aqueous NaOH solution (40 ml) and extracted three times with ether (60 ml×3). The combined organic layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After removal of solvent, the product was purified by distillation at 161° C., 0.3 mmHg and isolated in 85.5% (6.31 g) yield. 1H NMR (CDCl3, 500 MHz) δ ppm: 4.12 (s, 2H, CH2), 7.0-7.5 (m, 4H, Ar—H)GC-MS (relative intensity %): 278, 280 (1:1, 30.8, M+), 91(100, PhCH2+).

後処理

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. extractionextracted three times with ether (60 ml×3)
  3. washThe combined organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removal of solvent
  6. distillationthe product was purified by distillation at 161° C.
  7. custom0.3 mmHg and isolated in 85.5% (6.31 g)
  8. customyield

出典と根拠

ORDレコード
ord-fa2539ae0aa144ffbfe16bb40fbc5444
出典データセット
uspto-grants-2008_12
特許番号
US07459106B2

反応ノート

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