Lithium diisopropylamide → HCID 86693000, compound
Reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[O:7])=[C:4](C)[CH:3]=1.[Li+].CC([N-]C(C)C)C.[F:24][C:25]([F:33])([F:32])[C:26](N(OC)C)=[O:27]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]([CH2:9][CH3:10])[CH2:11][CH3:12])=[O:7])=[C:13]([C:26](=[O:27])[C:25]([F:24])([F:32])[F:33])[CH:14]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-bromo-N,N-diethyl-2-methylbenzamide (500 mg, 1.851 mmol) in Tetrahydrofuran (4.63 ml) was cooled to −78 C and treated with LDA (2.313 ml, 4.63 mmol) for 15 minutes before 2,2,2-trifluoro-N-methoxy-N-methylacetamide (320 mg, 2.036 mmol) in Tetrahydrofuran (4.63 ml) was added to the reaction mixture and allowed to warm to room temperature. The reaction was stirred overnight and then partitioned between 1N HCl (100 mL) and EtOAc (100 mL). The aqueous layer was further extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine (150 mL), dried over magnesium sulfate, filtered and concentrated. Purification using MPLC (0-20% EtOAc/Hex) affords 4-bromo-N,N-diethyl-2-(trifluoroacetyl)benzamide. LC-MS (IE, m/z): 366 [M+1]+.
Workup
- additionwas added to the reaction mixture
- custompartitioned between 1N HCl (100 mL) and EtOAc (100 mL)
- extractionThe aqueous layer was further extracted with EtOAc (2×50 mL)
- washThe combined organic layers were washed with brine (150 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customPurification
Sources & evidence
- ORD record
- ord-62fb2c407bcf485eae59db5b607f1c77
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056859B2
Reaction notes
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