4-Benzoyl-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one → 4-Benzoyl-1-(3-fluoro-4-hydroxyphenyl)pyrrolidin-2-one

HRID 1993386Notes

Reaction equation

HRID 1993386 reaction equation
[C:1]([CH:9]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]([F:22])[CH:15]=2)[C:11](=[O:23])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>B(Br)(Br)Br.C(Cl)Cl>[C:1]([CH:9]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([F:22])[CH:15]=2)[C:11](=[O:23])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 574454054-Benzoyl-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one

Product 1

HCID 574454064-Benzoyl-1-(3-fluoro-4-hydroxyphenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 22277759Boron tribromide dichloromethaneSolvent

Procedure

A mixture of 4-benzoyl-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one (Step 2, 1.0 g, 3.2 mmol) in 20 mL of 1 M BBr3/CH2Cl2 was stirred at RT for 16 h. The solution was concentrated in vacuo and the residue was diluted with 50 mL of MeOH and concentrated in vacuo again. The resulting white solid was washed with 50% EtOAc/hexane to give the title compound. MS (ESI pos. ion) m/z: 300.4 (M+H). Calc'd Exact Mass for C17H14FNO3: 299.3.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionthe residue was diluted with 50 mL of MeOH
  3. concentrationconcentrated in vacuo again
  4. washThe resulting white solid was washed with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-7d0ece2889824c4d80fdf5d50a9d8af8
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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