Sodium Carbonate → 2-Chloro-4-benzylnitrobenzene

HRID 1062404Notes

Reaction equation

HRID 1062404 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 222871592-Chloro-4-benzylnitrobenzeneYield 31.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-4799e3ea2d644d9dbf8fc2f14094fcf9
Source dataset
uspto-grants-2005_11
Patent number
US06960688B2

Reaction notes

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