alpha-Bromo-o-chlorotoluene → 3-(2-Chlorobenzyloxy)-5-methylphenol

HRID 651514Notes

Reaction equation

HRID 651514 reaction equation
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[H-].[Na+].[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Br>CN(C)C=O>[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][O:5][C:4]1[CH:3]=[C:2]([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=1

Participants

5

Reactant 3

HCID 11905alpha-Bromo-o-chlorotolueneHCID 24758Sodium hydrideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 158950973-(2-Chlorobenzyloxy)-5-methylphenolYield 28.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.31 g (9.22 mmol) of orcinol monohydrate in 20 mL anhydrous N,N-dimethylformamide under a nitrogen atmosphere was added 220 mg (9.17 mmol) of NaH (100%). After 5 min, 1.30 mL (10.0 mmol) of 2-chlorobenzyl bromide was added. The reaction mixture was stirred for 2 H and then quenched with 1 N HCl. The reaction mixture was extracted into ethyl acetate (200 mL). The organic phase was washed with water (4×100 mL), dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (diethyl ether/hexane (50:50 to 1.00:0) gave 656 mg of the title compound as a glass.

Workup

  1. customquenched with 1 N HCl
  2. extractionThe reaction mixture was extracted into ethyl acetate (200 mL)
  3. washThe organic phase was washed with water (4×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (diethyl ether/hexane (50:50 to 1.00:0)

Sources & evidence

ORD record
ord-518c13a2a12a44d3b0ed23df55f34af2
Source dataset
uspto-grants-2001_08
Patent number
US06281206B1

Reaction notes

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