Boron tribromide → 3-(1-Pyrrolidinyl)phenol

HRID 902706Notes

Reaction equation

HRID 902706 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>ClCCl>[N:9]1([C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 112175611-(3-methoxyphenyl)pyrrolidine

Product 1

HCID 1176643-(1-Pyrrolidinyl)phenolYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 1-(3-methoxy-phenyl)-pyrrolidine (354 mg, 2 mmol) in dichloromethane (30 ml) at 0° C. was added BBr3 (4.0 ml, 4 mmol, 1 M solution in dichloromethane) in a dropwise fashion. The resulting solution was stirred over night at room temperature and then poured into ice water (30 ml). The aqueous mixture was extracted with dichloromethane (3×). The combine organic layers were washed with brine (1×), dried over sodium sulfate, and filtered. The dichloromethane filtrate was concentrated to afford the title compound as an oil (317 mg, 97%). MS(ES) m/e 164.2 ([M+H]+).

Workup

  1. extractionThe aqueous mixture was extracted with dichloromethane (3×)
  2. washThe combine organic layers were washed with brine (1×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe dichloromethane filtrate was concentrated

Sources & evidence

ORD record
ord-eb0e15b0723d43848a6d6cb02d9b30c2
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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