Bromide ion → HCID 59701029, compound
Reaction equation
[F:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].CN(CCN(C)C)C.[Li][CH:21]([CH2:23][CH3:24])[CH3:22].[Br-:25].[CH2:26]1[CH2:30][O:29][CH2:28][CH2:27]1>>[Br:25][C:21]1[CH:23]=[CH:24][C:28]([O:29][CH3:30])=[C:27]([CH2:26][CH2:11][C:3]2[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:4]=2[C:5]([OH:7])=[O:6])[CH:22]=1Participants
Procedure
A solution of 3-fluoro-2-methylbenzoic acid (5.0 g, 1.0 equiv) in THF (175 mL) was cooled to −78° C. under an atmosphere of argon. TMEDA (9.86 mL, 2.0 equiv) was added via syringe. s-BuLi (1.4 M in cyclohexane, 49 mL, 2.1 equiv) was added dropwise via addition funnel over 30 min. After stirring for 2.5 hr, the bromide (13.7 g, 1.5 equiv) in THF (25 mL) was added dropwise. Upon completion of the addition, the solution was allowed to stir and warm to room temperature overnight. The reaction was quenched by the addition of water and then diluted with hexanes. The aqueous and organic phases were separated and the organic phase was washed with water. The aqueous phase was acidified to pH=1 with 1N HCl and then extracted with EtOAc. The resulting organic solution was dried over Na2SO4, filtered and concentrated. The residue was rinsed with dichloromethane, filtered, and dried to give the desired product (7.6 g, 66%).
Workup
- additionUpon completion of the addition
- stirringto stir
- customThe reaction was quenched by the addition of water
- additiondiluted with hexanes
- customThe aqueous and organic phases were separated
- washthe organic phase was washed with water
- extractionextracted with EtOAc
- dry with materialThe resulting organic solution was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- washThe residue was rinsed with dichloromethane
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-602dc42bf7b2409aaec1087569926728
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375125B2
Reaction notes
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