Propargyl bromide → 1-[(Prop-2-yn-1-yl)oxy]-2-(trifluoromethyl)benzene
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[CH:12]#[C:13][CH2:14]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:14]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:10])([F:11])[F:1])[C:13]#[CH:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 2-(trifluoromethyl)phenol (50.0 g, 0.31 mol) and progargyl bromide (44.0 g, 0.37 mol) in ACN (500 mL) was added K2CO3 (51.0 g, 0.37 mol) and the mixture was stirred overnight at rt, concentrated, diluted with water and extracted with Et2O. The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by CC (PE/EA=40/1) to give compound P33a (59.7 g, 97%) as an oil.
Workup
- concentrationconcentrated
- additiondiluted with water
- extractionextracted with Et2O
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- custompurified by CC (PE/EA=40/1)
- customto give compound P33a (59.7 g, 97%) as an oil
Sources & evidence
- ORD record
- ord-7153c67ecf21467cbf3c81b45529fe39
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946446B2
Reaction notes
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