Sodium borohydride → HCID 86671392, compound

HRID 2403283Notes

Reaction equation

HRID 2403283 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([CH3:14])[CH:6]=1)=[O:4].ClCC(C1C=CC([N+]([O-])=O)=C(C)C=1)=O.[BH4-].[Na+].C[O-].[Na+]>C(O)C.CCOC(C)=O>[CH3:14][C:7]1[CH:6]=[C:5]([CH:3]2[CH2:2][O:4]2)[CH:10]=[CH:9][C:8]=1[N+:11]([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 58370509HCID 58370509, compoundHCID 80146944HCID 80146944, compound

Product 1

HCID 86671392HCID 86671392, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of the mixture of 2-bromo-1-(3-methyl-4-nitrophenyl)ethanone and 2-chloro-1-(3-methyl-4-nitrophenyl)ethanone (6.23 g) in ethanol (100 ml) at 5° C. was added portionwise over 5 min NaBH4 (913 mg). The reaction mixture was then stirred at room temperature for 1 hour to afford a dark yellow solution. TLC analysis showed the reaction was complete. Sodium methoxide (652 mg) was then added and the reaction mixture was stirred at room temperature overnight. TLC analysis showed a small amount of starting material remaining and so the reaction mixture was stirred at 40° C. for 1 h. The reaction mixture was then poured into EtOAc and extracted with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford (RS)-2-(3-methyl-4-nitrophenyl)oxirane (4.63 g, 94% over 2 steps) as a yellow oil. MS (EI): 179 (M+), 164 ([M-CH3]+), 162 [M-OH]+), 132 [M-OH—NO]+), 103, 77.

Workup

  1. customto afford a dark yellow solution
  2. stirringthe reaction mixture was stirred at room temperature overnight
  3. stirringso the reaction mixture was stirred at 40° C. for 1 h
  4. extractionextracted with saturated brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ec11e01cab84786a9d7129f263441bc
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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