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

HRID 2101747Notes

Reaction equation

HRID 2101747 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 (1.50 g, 7.39 mmol) (Bionet, CAS# 17332-11-5), 1-bromobutane (0.95 mL, 8.87 mmol) (Acros, CAS# 109-65-9), 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 C.2 (1.49 g, 78% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 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)
  5. customto afford compound C.2 (1.49 g, 78% yield) as a colorless oil

Sources & evidence

ORD record
ord-3056b8388c4e4f448893502b65c1d5ee
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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