Water → 4-(Benzyloxy)-2-bromo-1-methoxybenzene

HRID 1420685Notes

Reaction equation

HRID 1420685 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([Br:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:17])=[C:11]([Br:16])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 109788072-Bromo-4-(phenylmethoxy)phenol

Product 1

HCID 127274994-(Benzyloxy)-2-bromo-1-methoxybenzeneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-benzyloxy-2-bromophenol (20 g, 71.6 mmol) in N,N-dimethylformamide (65 ml) was added potassium carbonate (12.4 g, 89.6 mmol) and methyl iodide (12.7 g, 89.6 mmol). The mixture was stirred at room temperature for 18 hours, poured into water (250 ml) and extracted with ethyl acetate (2×100 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo to give the title compound (20.15 g, 96%), δH (250 MHz, CDCl3) 3.84 (3H, s, ArOCH3), 4.99 (2H, s, OCH2), 6.80-6.94 (2H, m ArH), 7.21 (1H, d, J 2.75Hz, ArH), 7.28-7.43 (5H, m).

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-08850a43c7474b3fa0c321dc1a35a3fd
Source dataset
uspto-grants-2000_06
Patent number
US06071928

Reaction notes

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