3,4-Dichlorophenol → HCID 59514717, compound
Reaction equation
[CH3:1][C:2]([OH:6])([C:4]#[CH:5])[CH3:3].C1CCN2C(=NCCC2)CC1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:31][C:32]1[CH:33]=[C:34](O)[CH:35]=[CH:36][C:37]=1[Cl:38]>C(#N)C>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([O:6][C:2]([CH3:3])([CH3:1])[C:4]#[CH:5])=[CH:36][C:37]=1[Cl:38]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-Methyl-but-3-yn-2-ol (1.68 g, 20 mmol) in acetonitrile (10 ml) was treated with DBU (20 mmol) and trifluoroacetic anhydride (20 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 20 mins and then transferred to the solution of 3,4-dichlorophenol in acetonitrile (15 ml) with DBU (22 mmol) and CuCl2.H2O (10 mg) at the same temperature over a period of about 10 mins. The reaction mixture was stirred for 2 h and then quenched with H2O. Ethyl acetate was added to extract the product twice. Organic layer was washed with brine, dried and concentrated to yield the title compound as a colorless liquid.
Workup
- stirringThe reaction mixture was stirred for 2 h
- customquenched with H2O
- additionEthyl acetate was added
- extractionto extract the product twice
- washOrganic layer was washed with brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e42de6b7763d40b79822f769f642dab4
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812183B2
Reaction notes
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