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

HRID 1169941Notes

Reaction equation

HRID 1169941 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 ml, 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 h before 1,3-dibromo-5-fluorobenzene (15.9 g, 62.5 mmol) was added. The reaction was stirred at room temperature for 12 h. 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 (1M 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 (1M aq)
  5. dry with materialwater, brine, dried (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-dd6064b1e5e9420cbeec7bc8349c6de1
Source dataset
uspto-grants-2010_11
Patent number
US07825160B2

Reaction notes

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