Water → 1-Bromo-2-(methoxymethoxy)benzene

HRID 1356523Notes

Reaction equation

HRID 1356523 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[CH3:11][O:12][CH2:13]Br.O>CN(C=O)C>[CH3:11][O:12][CH2:13][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[Br:3]

Participants

6

Reactant 4

HCID 962WaterHCID 72442-BromophenolHCID 24758Sodium hydrideHCID 83093Bromomethyl methyl ether

Product 1

HCID 113104791-Bromo-2-(methoxymethoxy)benzeneYield 53.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of sodium hydride (1.2 g, 52.1 mmol, 60% dispersion in mineral oil) in DMF (75 mL) at 0° C. was added 2-bromophenol (6.0 g, 34.7 mmol) dropwise. After stirring for 20 min, bromomethyl methyl ether (4.3 g, 34.7 mmol) was added. After stirring for 16 h at room temperature, the mixture was poured into water (250 mL) and extracted with hexane. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography (silica gel, hexane) to yield the title compound as a colorless oil (4.0 g, 53%). 1HNMR (400 MHz, CDCl3) δ7.55 (d, 1H), 7.28 (t, 1H), 7.16 (d, 1H), 6.91 (t, 1H), 5.25 (s, 2H), 3.54 (s, 3H).

Workup

  1. stirringAfter stirring for 16 h at room temperature
  2. extractionextracted with hexane
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel, hexane)

Sources & evidence

ORD record
ord-2cfdeea2c58f42d4ac5d7ca2749daae1
Source dataset
uspto-grants-2003_07
Patent number
US06586466B2

Reaction notes

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