Boron tribromide → 5-Bromo-5-phenylpentan-1-ol

HRID 550339Notes

Reaction equation

HRID 550339 reaction equation
B(Br)(Br)[Br:2].[C:5]1([CH:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>ClCCl>[Br:2][CH:11]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:12][CH2:13][CH2:14][CH2:15][OH:16]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 2638501-Phenylpentane-1,5-diol

Product 1

HCID 669877265-Bromo-5-phenylpentan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1.2 mL, 12.69 mol) was slowly added to a dichloromethane solution (40 mL) of 1-phenylpentane-1,5-diol (1.89 g, 10.52 mmol) at 0° C. The reaction mixture was stirred for one hour and quenched with water. The aqueous layer was extracted with dichloromethane (3×10 mL), and the combined organics were dried (magnesium sulfate). The residue was purified by column chromatography on silica gel, eluting with 0-100% ethyl acetate/hexanes to give the title compound as a yellow oil. 1H NMR (500 MHz, CDCl3) δ 1.33-1.44 (m, 1H), 1.52-1.70 (m, 2H), 1.90-2.00 (m, 1H), 2.13-2.22 (m, 1H), 2.27-2.36 (m, 1H), 3.65 (t, J=6.3 Hz, 2H), 4.96 (dd, J=6.9, 8.0 Hz, 1H), 7.24-7.30 (m, 1H), 7.33 (t, J=7.8 Hz, 2H), 7.39 (d, J=7.1 Hz, 2H).

Workup

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with dichloromethane (3×10 mL)
  3. dry with materialthe combined organics were dried (magnesium sulfate)
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with 0-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bd791e56b7804c0d8c26f4cd2e843c4a
Source dataset
uspto-grants-2011_05
Patent number
US07947664B2

Reaction notes

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