Butyl bromide → 2-Bromo-1-butoxy-4-methoxybenzene

HRID 1662314Notes

Reaction equation

HRID 1662314 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].Br[CH2:12][CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[O:10][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 10796Cesium carbonateHCID 2973822-Bromo-4-methoxyphenol

Product 1

HCID 578018162-Bromo-1-butoxy-4-methoxybenzeneYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-bromo-4-methoxyphenol (available from Betapharma Inc.) (1.50 g, 7.39 mmol), 1-bromobutane (available from Aldrich) (0.95 mL, 8.87 mmol), and cesium carbonate (3.13 g, 9.60 mmol) in DMF (40 mL) was stirred overnight at room temperature. The mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4, and concentrated. The crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford compound 4.1 (1.49 g, 78% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.15 (d, J=2.7 Hz, 1H), 6.84 (d, J=9.0 Hz, 1H), 6.80 (dd, J=3.1, 9.0 Hz, 1H), 3.97 (t, J=6.5 Hz, 2H), 3.76 (s, 3H), 1.79 (m, 2H), 1.53 (m, 2H), 0.98 (t, J=7.2 Hz, 3H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-d1b94e93ce5f4ddfa244108e79656823
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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