Sodium Carbonate → 2-Chloro-4-benzylnitrobenzene

HRID 2301060ノート

反応式

HRID 2301060 の反応式
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.C([SiH](CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C(O)(C(F)(F)F)=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH2:7][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 347783(3-Chloro-4-nitrophenyl)(phenyl)methanoneHCID 4311764Sodium borohydride

生成物 1

HCID 222871592-Chloro-4-benzylnitrobenzene収率 31.7%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

Sodium borohydride (1.45 g) was added to a solution of 3-chloro-4-nitrobenzophenone (2.0 g) (prepared as described by R. B. Davis and J. D. Benigni, J. Org. Chem., 1962. 27, 1605) in ethanol and the mixture was stirred for 18 hours. Volatile material was removed by evaporation and the residue was suspended in water (100 ml) and cautiously acidified with dilute aqueous hydrochloric acid (50 ml) and stirred a further 2 hours. The reaction mixture was basified with 2M aqueous sodium hydroxide solution and extracted with DCM. The extracts were combined, dried and concentrated by evaporation to give an oil. This was dissolved in TFA (12.1 ml) with cooling with an ice bath then treated dropwise with triethylsilane (5.05 ml) and stirred overnight. The reaction mixture was poured onto aqueous sodium carbonate solution and extracted with DCM. The extracts were combined, dried and evaporated to give an oil which was purified by chromatography eluting with 20-50% ethyl acetate/hexane to give the title compound (0.60 g) as an oil. NMR (CDCl3): 4.0 (s, 3H), 7.1-7.4 (m, 8H); MS (CI): 247 (M+).

後処理

  1. customVolatile material was removed by evaporation
  2. stirringstirred a further 2 hours
  3. extractionextracted with DCM
  4. customdried
  5. concentrationconcentrated by evaporation
  6. customto give an oil
  7. temperaturewith cooling with an ice bath
  8. stirringstirred overnight
  9. extractionextracted with DCM
  10. customdried
  11. customevaporated
  12. customto give an oil which
  13. customwas purified by chromatography
  14. washeluting with 20-50% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-a0ac85cfc5ee492785a87902f73b2c97
出典データセット
uspto-grants-2002_12
特許番号
US06498275B1

反応ノート

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