Hydrogen Peroxide → 2-Ethoxy-5-fluorophenol
Reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][CH3:11].[Li]CCCC.C[O:18]B(OC)OC.OO>C1COCC1.O.C(O)(=O)C>[CH2:10]([O:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[OH:18])[CH3:11]Participants
8
Conditions
- Temperature
- -75 °C
Procedure
The 2-bromo-1-ethoxy-4-fluoro-benzene (3.1 g) described in example 1.1 was dissolved in THF (25 ml). The solution was cooled to −75° C. and a solution of n-BuLi (9.73 ml, 1.6 M in hexane) was added slowly. The mixture was stirred for 30 min at −75° C. Trimethylborate (1.62 g) was added within 5 min. Acetic acid (1.27 g) and a 30% solution of H2O2 (1.51 g) were added sequentially. The mixture was stirred for 30 min at 0° C. and for 3 h at room temperature. Water was added and the mixture was extracted with ethyl acetate. The crude product was purified by column chromatography (n-hexane/ethyl acetate) to yield 1.77 g of 2-ethoxy-5-fluoro-phenol as a colorless oil. MS: 156 ([M]+).
Workup
- stirringThe mixture was stirred for 30 min at 0° C. and for 3 h at room temperature
- extractionthe mixture was extracted with ethyl acetate
- customThe crude product was purified by column chromatography (n-hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-167901e42cab442d99dce4238feb8351
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06548694B2
Reaction notes
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