tert-Butyl methyl ether → 2-(4-Bromo-3-fluorophenyl)oxirane
Reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([F:12])[CH:6]=1)=[O:4].[BH4-].[Na+].C[O-].[Na+].COC(C)(C)C>C(O)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[F:12]Participants
6
Conditions
- Temperature
- 5 °C
Procedure
2-Bromo-1-(4-bromo-3-fluorophenyl)-ethanone [CAS 1003879-02-4] (32.3 g, 109 mmol) was dissolved in ethanol (250 ml). The reaction mixture was cooled to 5° C. to give a yellow suspension. Sodiumborohydride (4.13 g, 109 mmol) was added over 5 min. The reaction mixture was stirred at room temperature for 1 hour. Sodium methoxide (2.95 g, 54.6 mmol) was added. The reaction mixture was stirred at 50° C. for 6 h. The reaction mixture was poured into tert.butyl methyl ether and extracted with brine. The organic layer was dried over MgSO4 and concentrated in vacuo to yield a yellow oil (25.1 g, 94%). GC-EI-MS: 216 ([M.+]).
Workup
- customto give a yellow suspension
- stirringThe reaction mixture was stirred at 50° C. for 6 h
- extractionextracted with brine
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2164d6e0025041118813a0d34858a602
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181230B2
Reaction notes
Loading…