Benzyl Alcohol → 1-(Benzyloxy)-3,5-dibromobenzene

HRID 226499Notes

Reaction equation

HRID 226499 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:11][C:12]1[CH:17]=[C:16](F)[CH:15]=[C:14]([Br:19])[CH:13]=1.O>C1COCC1>[CH2:1]([O:8][C:16]1[CH:17]=[C:12]([Br:11])[CH:13]=[C:14]([Br:19])[CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 1370031,3-Dibromo-5-fluorobenzene

Product 1

HCID 147841501-(Benzyloxy)-3,5-dibromobenzeneYield 104%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzylalcohol (9.7 mLl, 94 mmol) was added dropwise to a suspension of NaH (4.0 g of a 60% suspension in mineral oil, 100 mmol) in THF (150 mL) at room temperature and the mixture was stirred at room temperature for 1 hour before 1,3-dibromo-5-fluorobenzene (15.9 g, 62.5 mmol) was added. The reaction was stirred at room temperature for 12 hours. Water was added carefully and the THF was evaporated under reduced pressure. The residue was extracted with iso-hexane (×3) and the combined organic extracts were washed with NaOH solution (1 M aq.), water, brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (EtOAc:petroleum ether) to give 1-benzyloxy-3,5-dibromobenzene (14.7 g, 65 mmol) as a colourless liquid in 69% yield. 1H NMR (CDCl3) δ 7.45-7.33 (m, 5H), 7.30-7.28 (m, 1H), 7.10-7.08 (m, 2H), 5.02 (s, 2H).

Workup

  1. additionwas added
  2. customthe THF was evaporated under reduced pressure
  3. extractionThe residue was extracted with iso-hexane (×3)
  4. washthe combined organic extracts were washed with NaOH solution (1 M aq.), water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography (EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-c299f7e452564eac9193d5330d095664
Source dataset
uspto-grants-2009_07
Patent number
US07557244B2

Reaction notes

Loading…