Water → 2-Bromo-6-methylanisole

HRID 564457

Reaction equation

HRID 564457 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[H-].[Na+].[CH3:12]OS(OC)(=O)=O.O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 110953292-Bromo-6-methylphenol

Product 1

HCID 122626482-Bromo-6-methylanisoleYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-6-methylphenol (34.6 g, 0.18 mol) in THF (300 mL), NaH (9.6 g, 0.24 mol, 60%) was added in several portions. After the mixture was stirred for 1 h, Me2SO4 (28.0 g, 0.22 mol) was added dropwise, then the mixture was stirred over night. H2O (50 mL) was added, and the solvent was removed under reduced pressure. Then the residue was dissolved in Et2O (250 mL), and was washed with NaOH (5%, 100 mL), brine (100 mL), and dried with Na2SO4. After removing the solvent, 35.3 g of the crude product was obtained. (Yield: 95%). 1H NMR (400 MHz, CDCl3) δ 2.33 (s, 3 H), 3.81 (s, 3 H), 6.88 (t, J=8.0 Hz, 1H), 7.10 (d, J=8.0 Hz, 1 H), 7.30 (d, J=7.6 Hz, 1 H).

Workup

  1. stirringthe mixture was stirred over night
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThen the residue was dissolved in Et2O (250 mL)
  4. washwas washed with NaOH (5%, 100 mL), brine (100 mL)
  5. dry with materialdried with Na2SO4
  6. customAfter removing the solvent

Sources & evidence

ORD record
ord-06cf27d79b3d452881ae6c92a7727acb
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Linked notes

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