Benzyl [2-(4-acetylphenoxy)ethyl]carbamate → Benzyl-[2-(4-bromoacetylphenoxy)-ethyl]-carbamate

HRID 413302Notes

Reaction equation

HRID 413302 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-:24].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.CO>[CH2:1]([O:8][C:9](=[O:23])[NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH2:21][Br:24])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 19889128Benzyl [2-(4-acetylphenoxy)ethyl]carbamateHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 12986050Benzyl-[2-(4-bromoacetylphenoxy)-ethyl]-carbamateYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Benzyl-[2-(4-acetyl-phenoxy)-ethyl]-carbamate (10.2 g, 32.5 mmol) was dissolved in methylene chloride (100 ml) and methanol (50 ml), and tetrabutylamonium tribromide (15.7 g, 32.5 mmol) was added in one portion. The reaction mixture was stirred for about sixteen hours, and then quenched with water. The aqueous phase was extracted with ethyl acetate and then washed with saturated aqeous sodium bicarbonate, and saturated Na2S2O3. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo, and the resulting crude material was purified by column chromatography (silica gel; hexanes to 2:1 hexanes/ethyl acetate) to afford a colorless oil which solidified upon standing. (11.5 g, 90% yield).

Workup

  1. customquenched with water
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washwashed with saturated aqeous sodium bicarbonate, and saturated Na2S2O3
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe resulting crude material was purified by column chromatography (silica gel; hexanes to 2:1 hexanes/ethyl acetate)
  8. customto afford a colorless oil which

Sources & evidence

ORD record
ord-3c1b8d842502498b9b20d44a9e878581
Source dataset
uspto-grants-2003_05
Patent number
US06566377B2

Reaction notes

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