Tetra-n-butylammonium tribromide → 2-Bromo-1-(4-hydroxymethyl-2-methyl-phenyl)-ethanone

HRID 1425735Notes

Reaction equation

HRID 1425735 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[C:5]([CH3:12])[CH:4]=1.[Br-:13].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[Br:13][CH2:10][C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][C:5]=1[CH3:12])=[O:11]

Participants

4

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 866955361-(4-Hydroxymethyl-2-methyl-phenyl)-ethanone

Product 1

HCID 866955352-Bromo-1-(4-hydroxymethyl-2-methyl-phenyl)-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-hydroxymethyl-2-methyl-phenyl)-ethanone (preparation 1a, 600 mg, 3.65 mmol) in CH2Cl2 (25 mL) is added tetrabutylammonium tribromide in several portions (1.76 g, 3.65 mmol). The reaction mixture is stirred for 30 min at room temperature. After washing with water, the organic layer is dried over MgSO4 and concentrated under reduced pressure. The remaining residue is dissolved in hexanes/EtOAc 3:7 and filtered over silica gel.

Workup

  1. washAfter washing with water
  2. dry with materialthe organic layer is dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe remaining residue is dissolved in hexanes/EtOAc 3:7
  5. filtrationfiltered over silica gel

Sources & evidence

ORD record
ord-1e8300fe07e842c09e8c9d688bcb8d5e
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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