Benzene, 1-bromo-2-(trifluoromethyl)- → HCID 66691009, compound

HRID 513021Notes

Reaction equation

HRID 513021 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9].[Li]CCCC.[O:17]=[C:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>C1COCC1.CCCCCC>[OH:17][C:18]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]([F:11])([F:10])[F:9])[CH2:22][CH2:21][CH2:20][N:19]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]

Participants

6

Reactant 3

HCID 9806Benzene, 1-bromo-2-(trifluoromethyl)-HCID 3790001-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl esterHCID 178418339Butyllithium

Product 1

HCID 66691009HCID 66691009, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-bromo-2-(trifluoromethyl)benzene (0.27 mL, 2.0 mmol) in THF (5 mL) at −78° C. was added nBuLi (0.72 mL of a 2.8 M solution in Hexane, 2.0 mmol). The reaction was stirred at −78° C. for 15 minutes then added to a solution of tert-butyl 2-oxopyrrolidine-1-carboxylate (0.33 mL, 2.0 mmol) in THF (5 mL) at −78° C. The reaction was stirred to room temperature over 1 hour, quenched with saturated aqueous ammonium chloride and diluted with EtOAc. The organic layer was separated, dried over magnesium sulfate, filtered and reduced to dryness to afford tert-butyl 2-hydroxy-2-(2-(trifluoromethyl)phenyl)pyrrolidine-1-carboxylate (I-27) as a clear oil. MS m/z 276.1 (M−55)+.

Workup

  1. stirringThe reaction was stirred to room temperature over 1 hour
  2. customquenched with saturated aqueous ammonium chloride
  3. additiondiluted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-26e263b33af142579559e06c183aaef2
Source dataset
uspto-grants-2015_08
Patent number
US09102671B2

Reaction notes

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