Bromoacetyl bromide → 136382-01-9

HRID 1484710Notes

Reaction equation

HRID 1484710 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][CH2:6][C:7](Br)=[O:8].[CH3:10][O:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1>C(Cl)Cl>[Br:5][CH2:6][C:7]([C:13]1[C:14]([CH3:19])=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=1[O:11][CH3:10])=[O:8].[Br:5][CH2:6][C:7]([C:15]1[C:16]([CH3:18])=[CH:17][C:12]([O:11][CH3:10])=[CH:13][C:14]=1[CH3:19])=[O:8]

Participants

6

Reactant 3

HCID 61147Bromoacetyl bromideHCID 701263,5-DimethylanisoleHCID 6451240Aluminum(III) Chloride

Product 2

HCID 15725275136382-01-9Yield 31.7%HCID 58442455HCID 58442455, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
2.5 °C

Procedure

To a mixture of AlCl3 (2.0 g, 14.7 mmol) in CH2Cl2 (12 mL) was added a solution of 2-bromoacetyl bromide (3.0 g, 14.9 mmol) in CH2Cl2 (2 mL) at 0° C. Then, a solution of 1-methoxy-3,5-dimethylbenzene (2.0 g, 14.7 mmol) in CH2Cl2 (2 mL) was added dropwise. The whole mixture was stirred for 1.5 h at 0 to 5° C. After that, the mixture was poured into ice water (100 g). The mixture was extracted with CH2Cl2 (3×30 mL). The combined organic phases were dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo and the residue was purified by silica gel column (hexane/EtOAc=40/1 to 25/1) to afford 2-bromo-1-(2-methoxy-4,6-dimethylphenyl)ethanone (1.20 g, 31.7%) and 2-bromo-1-(4-methoxy-2,6-dimethylphenyl) ethanone (250 mg, 6.6%).

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (3×30 mL)
  2. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  3. filtrationAfter filtration
  4. customthe solvent was removed in vacuo
  5. customthe residue was purified by silica gel column (hexane/EtOAc=40/1 to 25/1)

Sources & evidence

ORD record
ord-9f2a3e5e7df34a73bae81a45cd7e8ca2
Source dataset
uspto-grants-2016_08
Patent number
US09422275B2

Reaction notes

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