Benzyl Bromide → HCID 14631589, compound

HRID 1453315Notes

Reaction equation

HRID 1453315 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:15][C:16]1C=[CH:20][C:19](O)=[C:18]([CH2:23][CH3:24])[CH:17]=1>CN(C=O)C>[CH2:7]([O:4][C:1]1[CH:20]=[CH:19][C:18]([CH2:23][CH3:24])=[CH:17][C:16]=1[Br:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 878774-Bromo-2-ethylphenol

Product 1

HCID 14631589HCID 14631589, compoundYield 569.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (21.6 g, 0.16 mol) followed by benzyl bromide (6.2 mL, 52 mmol) were added to a solution of 4-bromo-2-ethyl-phenol (1.6 g, 7.9 mmol, from step 1 of Example B(98)) in DMF (75 mL). The mixture was stirred for 20 hours and then partitioned between 1N HCl and EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated. The crude yellow oil was purified by flash column chromatography (hexanes) to give the desired product (13.1 g, 87%). 1H NMR (400 MHz, CDCl3): δ 1.20 (t, J=7.6 Hz, 3H), 2.56 (q, J=7.8 Hz, 2H), 5.13 (s, 2H), 6.84 (d, J=8.3 Hz, 1H), 7.04 (dd, J=8.3, 2.3 Hz, 1H), 7.32 (m, 1H), 7.38 (m, 3H), 7.47 (d, J=7.9 Hz, 2H).

Workup

  1. custompartitioned between 1N HCl and EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude yellow oil was purified by flash column chromatography (hexanes)

Sources & evidence

ORD record
ord-0cf76d229e6c4dcaa493e14794b5338b
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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