3-Methyl-1-(4-methylphenyl)butan-1-one → HCID 59828861, compound

HRID 1190946Notes

Reaction equation

HRID 1190946 reaction equation
CC(C)CC(C1C=CC(C)=CC=1)=O.[Br:14][CH2:15][C:16]1(CBr)[CH:21]=[CH:20][C:19]([C:22](=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:18][CH2:17]1>>[Br:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:27])[CH2:23][CH:24]([CH3:25])[CH3:26])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 125064723-Methyl-1-(4-methylphenyl)butan-1-oneHCID 86624157HCID 86624157, compound

Product 1

HCID 59828861HCID 59828861, compound

Procedure

Add NBS (1.6 g, 9.2 mmol) to a solution of 3-methyl-1-p-tolyl-butan-1-one (1.5 g, 8.4 mmol) and AIBN (1.4 g, 8.4 mmol) in carbon tetrachloride (30 mL) and heat to reflux for 18 h. Cool the reaction mixture to room temperature and pour into water (500 mL). Extract with EtOAc (3×100 mL), wash the combined organic extracts with brine (300 mL), dry over Na2SO4 and concentrate in vacuo to obtain 2.9 g of a brown oil, consisting of the desired intermediate with a small amount of unreacted 3-methyl-1-p-tolyl-butan-1-one and 1-(4,4-dibromomethyl-phenyl)-3-methyl-butan-1-one. Use this mixture in the next step without additional purification. MS (APCI+) m/z: 255 (M+).

Workup

  1. customUse this mixture in the next step without additional purification

Sources & evidence

ORD record
ord-314b3a59c9d649378ca06fb92d482176
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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