Benzene, 1-bromo-3-(trifluoromethyl)- → HCID 65916912, compound
Reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1.[O:17]1[C:21]2([CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)[O:20][CH2:19][CH2:18]1>C1COCC1>[F:14][C:13]([F:16])([F:15])[C:9]1[CH:8]=[C:7]([C:24]2([OH:27])[CH2:25][CH2:26][C:21]3([O:20][CH2:19][CH2:18][O:17]3)[CH2:22][CH2:23]2)[CH:12]=[CH:11][CH:10]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a round bottom flask was added n-BuLi (3.84 mL, 9.60 mmol) at −78° C. under argon. THF (10 mL) was added followed by addition of 1-bromo-3-(trifluoromethyl)benzene (0.884 mL, 6.40 mmol) in THF (1 mL). The reaction mixture was stirred for 30 minutes at −78° C. A solution of 1,4-dioxaspiro[4.5]decan-8-one (1.00 g, 6.40 mmol) in THF (5 mL) was then added dropwise to the reaction mixture at −70° C. The reaction was stirred for 1 h at −70° C., and then quenched by the addition of 1 N HCl. The reaction mixture was extracted with EtOAc and the organic portions were separated and combined. The organic layer was dried over Na2SO4, filtered, and concentrated to give Intermediate 3A (1.87 g, 6.19 mmol, 97.0% yield). LCMS=325 [M+Na], RT=1.89 minutes (Method B).
Workup
- stirringThe reaction was stirred for 1 h at −70° C.
- customquenched by the addition of 1 N HCl
- extractionThe reaction mixture was extracted with EtOAc
- customthe organic portions were separated
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ec5007e2bcec4a0283810412d317a3ce
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09199946B2
Reaction notes
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