tert-Butyl methyl ether → HCID 86671405, compound

HRID 571816Notes

Reaction equation

HRID 571816 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9]Cl)=[CH:4][C:3]=1[Cl:12].[BH4-].[Na+].C[O-].[Na+].CC(OC)(C)C>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][O:11]2)=[CH:4][C:3]=1[Cl:12]

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 533503271261859-54-4

Product 1

HCID 86671405HCID 86671405, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-(4-bromo-3-chlorophenyl)-2-chloroethanone (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 light 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 extracted with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford (RS)-2-(4-bromo-3-chlorophenyl)oxirane (15.2 g) as a brown oil which was used in the next step without further purification.

Workup

  1. customto afford a light yellow solution
  2. stirringthe reaction mixture was stirred at 50° C. for 4 h
  3. extractionextracted with saturated brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-97e01c335dd94e538c74f25fe496f489
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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