Dimethylformamide → 4-Bromo-2-ethyl-1-methoxymethyl-benzene

HRID 859680Notes

Reaction equation

HRID 859680 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH2:10][CH3:11])[CH:3]=1.[H-].[Na+].[CH3:14]N(C=O)C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH3:14])=[C:4]([CH2:10][CH3:11])[CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 587642724-Bromo-2-ethylbenzenemethanol

Product 1

HCID 587640534-Bromo-2-ethyl-1-methoxymethyl-benzeneYield 69%

Procedure

To a solution of (4-bromo-2-ethyl-phenyl)-methanol (0.700 g, 3.25 mmol) in DMF (30 mL) was added NaH (0.156 g, 60% dispersion in mineral oil, 3.90 mmol) followed by Mel (0.22 mL, 3.58 mmol). The mixture was stirred for 16 hours and then partitioned between H2O and EtOAc. The aqueous layer was extracted with EtOAc, and the organic layer was washed with brine, dried over Na2SO4, and concentrated to a yellow oil. Purification by flash column chromatography (0% to 4% EtOAc in hexanes) gave the product as a clear oil (0.51 g, 69%). 1H NMR (300 MHz, CDCl3): δ 1.15 (t, J=7.6 Hz, 3 H), 2.58 (q, J=7.5 Hz, 2 H), 3.32 (s, 3 H), 4.35 (s, 2 H), 7.12 (m, 1 H), 7.24 (m, 1 H), 7.27 (d, J=2.1 Hz, 1 H).

Workup

  1. custompartitioned between H2O and EtOAc
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to a yellow oil
  6. customPurification by flash column chromatography (0% to 4% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ee767b73fc444537a77d147ee771ce73
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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