Sodium borohydride → HCID 86671405, compound

HRID 2403314Notes

Reaction equation

HRID 2403314 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([Cl:12])[CH:6]=1)=[O:4].ClCC(C1C=CC(Br)=C(Cl)C=1)=O.[BH4-].[Na+].C[O-].[Na+]>C(O)C.CC(OC)(C)C>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([CH:3]2[CH2:2][O:4]2)=[CH:6][C:7]=1[Cl:12]

Participants

7

Reactant 4

HCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 533503271261859-54-4HCID 583023292-Bromo-1-(4-bromo-3-chlorophenyl)ethan-1-one

Product 1

HCID 86671405HCID 86671405, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a stirred solution of the mixture of 2-bromo-1-(4-bromo-3-chlorophenyl)ethanone and 2-chloro-1-(4-bromo-3-chlorophenyl)ethanone (18.4 g) in ethanol (200 ml) at 5° C. was added portionwise over 5 min NaBH4 (2.23 g). The reaction mixture was then stirred at room temperature for 90 min to afford a yellow solution. TLC analysis showed the reaction was complete. Sodium methoxide (1.59 g) was then added and the reaction mixture was stirred at 50° C. for 4 h. TLC analysis showed the reaction was complete. The reaction mixture was then poured into TBME and washed with saturated brine. The organic layer was separated, then dried over Na2SO4 and concentrated in vacuo to afford (RS)-2-(4-bromo-3-chloro-phenyl)-oxirane (15.2 g) as a brown oil which was used in the next step without further purification.

Workup

  1. customto afford a yellow solution
  2. stirringthe reaction mixture was stirred at 50° C. for 4 h
  3. washwashed with saturated brine
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d3a2d8143614f579a8c787d76ffc837
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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