Water → HCID 69085281, compound

HRID 594735Notes

Reaction equation

HRID 594735 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8]C)[C:3]=1[CH:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)[C:13](=[O:27])[CH:12]([CH3:28])[CH2:11]1.O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[CH:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:18][CH:17]=2)[C:13](=[O:27])[CH:12]([CH3:28])[CH2:11]1

Participants

4

Reactant 2

HCID 962WaterHCID 69082453HCID 69082453, compound

Product 1

HCID 69085281HCID 69085281, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cooled (−78° C.) solution of 5-(2-fluoro-6-methoxyphenyl)-3-methyl-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one (518 mg; 1.30 mmol) in anh. DCM (7 ml) was treated dropwise with a solution of boron tribromide BBr3 (1.0 M in DCM; 6.52 ml; 6.52 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 17 h. Water was added dropwise, and the separated aq. layer was extracted with DCM. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered and concentrated to dryness under reduced pressure affording 5-(2-fluoro-6-hydroxyphenyl)-3-methyl-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one. LC-MS (conditions A): tR=0.84 min.; [M+H]+: 383.89 g/mol.

Workup

  1. extractionthe separated aq. layer was extracted with DCM
  2. washThe mixed organic layers were washed with brine
  3. dry with materialdried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1a62c6d601124642aa5ee3b7f35391b7
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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