Hydrochloric Acid → Ethyl 3-(2,6-dichloro-4-trifluoromethylphenyl)-3-hydroxypropionate
Reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:8][C:9]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([Cl:21])[C:10]=1[CH:11]=[O:12].COB(OC)OC.Cl>O1CCCC1.[Zn].C(O)(=O)C>[Cl:8][C:9]1[CH:16]=[C:15]([C:17]([F:19])([F:20])[F:18])[CH:14]=[C:13]([Cl:21])[C:10]=1[CH:11]([OH:12])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
Ethyl bromoacetate (13.7 ml) was added to a suspension of 30.0 g of 2,6-dichloro-4-trifluoromethylbenzaldehyde (7), 50 ml of trimethoxyborane and 8.5 g of zinc powder in 50 ml of anhydrous tetrahydrofuran with vigorous stirring at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into a mixture of 100 ml of 10% hydrochloric acid and 10 ml of acetic acid, and the resulting mixture was filtered through Celite. The aqueous filtrate was neutralized with a 5% aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate, drying over anhydrous magnesium sulfate and concentration under reduced pressure, affording 40.7 g of the desired compound in the form of a pale green oil (quantitative crude yield).
Workup
- stirringthe mixture was stirred overnight
- filtrationthe resulting mixture was filtered through Celite
- extractionfollowed by extraction with ethyl acetate
- dry with materialdrying over anhydrous magnesium sulfate and concentration under reduced pressure
Sources & evidence
- ORD record
- ord-7ff1a59db04d47c99c73442c0d25a6a3
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05739083
Reaction notes
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