Water → 2-[3,4-Bis(difluoromethoxy)phenyl]ethanol
Reaction equation
[F:1][CH:2]([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH2:11])=[CH:6][C:5]=1[O:12][CH:13]([F:15])[F:14].B.[OH2:18].[OH-].[Na+]>C1COCC1>[F:14][CH:13]([F:15])[O:12][C:5]1[CH:6]=[C:7]([CH2:10][CH2:11][OH:18])[CH:8]=[CH:9][C:4]=1[O:3][CH:2]([F:16])[F:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 1,2-bis(difluoromethoxy)-4-vinylbenzene (10 g, 0.0431 mol; see step (iii) above) in 25 mL of THF was added, dropwise, borane-methyl sulfide complex (10 mmol; 10 mL of a 1 M solution in THF). The resulting mixture was stirred at 60° C. for 1 h, before being cooled to RT. Excess borane was decomposed by adding few drops of water and the resultant mixture refluxed for 1 h with 2 M NaOH (100 mL) 50% H2O2 (87 mL). The mixture was then extracted with dichloromethane, washed with water and then brine, and dried over sodium sulfate. Solvent evaporation under reduced pressure gave the sub-title compound as a pale yellow liquid. Yield: 6 g.
Workup
- temperaturebefore being cooled to RT
- extractionThe mixture was then extracted with dichloromethane
- washwashed with water
- dry with materialbrine, and dried over sodium sulfate
- customSolvent evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-dd9b3e48c6614fb7a1406b10408b226b
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07648985B2
Reaction notes
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