2,4-Difluorophenol → (S)-benzyl 4-(2,4-difluorophenoxy)-3-oxobutan-2-ylcarbamate
Reaction equation
Br[CH2:2][C:3](=[O:17])[C@@H:4]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:5].[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[OH:26].[F-].[K+]>CN(C=O)C.ClCCl.O>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[O:26][CH2:2][C:3](=[O:17])[C@@H:4]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:5]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
A mixture of (S)-benzyl 4-bromo-3-oxobutan-2-ylcarbamate (prepared according to R. V. Hoffman et al., J. Org. Chem. 2001, 66, 5790-5795) (600 mg, 2.00 mmol), 2,4-difluorophenol (312 mg, 2.40 mmol) and potassium fluoride (380 mg, 6.54 mmol) in DMF (4 mL) was stirred at r.t. for 17 h. Water (15 mL) and dichloromethane (3 mL) were added and the mixture was stirred for 30 min. The mixture was added to a phase separator. The water phase was once more stirred with dichloromethane (3 mL), and added to the phase separator. The organic phases were concentrated and the residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 3/1) to give the title compound as a white solid (658 mg, 94% yield).
Workup
- stirringthe mixture was stirred for 30 min
- additionThe mixture was added to a phase separator
- additionadded to the phase separator
- concentrationThe organic phases were concentrated
- customthe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 3/1)
Sources & evidence
- ORD record
- ord-9db79ff1d7424dd585781c09e1e73fed
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143290B2
Reaction notes
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