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

HRID 482100Notes

Reaction equation

HRID 482100 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=O)C>[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-methylphenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.31 g (9.22 [mmol) of Orcinol monohydrate in 20 mL anhydrous DMF under a nitrogen atmosphere was add ed 220 mg (9.17 mmol) of NaH (100%). After 5 min, 1.3 mL (100 mmol) of 2-chlorobenzyl bromide was added. The reaction mixture was stirred for 2 h and then quenched with 1N HCl. The reaction mixture was extracted into ethyl acetate (200 mL). The organic phase was washed with H2O (4×100 mL), dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (ether/hexane (50:50 to 100:0) gave 656 mg of the title compound as a hardened oil. 1H-NMR (300 MHz, CDCl3) δ 7.54 (dd, 1H, J=3, 7 Hz), 7.39 (dd, 1H, J=3, 7 Hz), 7.2 -7.3 (m, 2H), 6.41 (s, 1H), 6.29-6:30 (m, 2H), 5.29 (s, 2H), and 2.28 (s, 3H).

Workup

  1. customquenched with 1N HCl
  2. extractionThe reaction mixture was extracted into ethyl acetate (200 mL)
  3. washThe organic phase was washed with H2O (4×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (ether/hexane (50:50 to 100:0)

Sources & evidence

ORD record
ord-714094ae27334198b072f3b89ab24386
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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