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

HRID 368523

Reaction equation

HRID 368523 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 chormatography (diethyl ether/hexane (50:50 to 100:0) gave 656 mg of the title compound as a glass. 1H-NMR (300 MHz, CDCl3) δ 7.54 (dd, 1 H, J=3, 7 Hz), 7.39 (dd, 1 H, J=3, 7 Hz), 7.2-7.3 (m, 2 H), 6.41 (s, 1 H), 6.29-6.30 (m, 2 H), 5.29 (s, 2 H), and 2.28 (s, 3 H).

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 chormatography (diethyl ether/hexane (50:50 to 100:0)

Sources & evidence

ORD record
ord-534138dc3a3246bd81aebcca78b3ef51
Source dataset
uspto-grants-2000_10
Patent number
US06133315

Linked notes

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