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1-Bromo-2-methylpropane → 1-(2-Isobutoxy-5-methoxyphenyl)ethanone

HRID 16644
Notes
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Reaction equation

HRID 16644 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].[H-].[Na+].Br[CH2:16][CH:17]([CH3:19])[CH3:18]>CN(C)C=O>[CH2:16]([O:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11])[CH:17]([CH3:19])[CH3:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 697141-(2-Hydroxy-5-methoxyphenyl)ethan-1-one

Product 1

HCID 684362051-(2-Isobutoxy-5-methoxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 10 g (0.06 mol) of 2′-hydroxy-5′-methoxyacetophenone, 2.6 g (0.066 mol) of 60% sodium hydride and 150 ml of dimethylformamide is heated for one hour at 80° C. 7.2 ml (0.066 mol) of 1-bromo-2-methylpropane are added dropwise. The mixture is heated for ten hours at 80° C. and is then poured into ice-water and extracted with ether. The ether solution is washed with normal sodium hydroxide solution. The dried (Na2SO4) organic phase is evaporated under reduced pressure (8.2 g; 62%).

Workup

  1. temperatureThe mixture is heated for ten hours at 80° C.
  2. extractionextracted with ether
  3. washThe ether solution is washed with normal sodium hydroxide solution
  4. dry with materialThe dried (Na2SO4) organic phase
  5. customis evaporated under reduced pressure (8.2 g; 62%)

Sources & evidence

ORD record
ord-019353d7e69c489b850181b2c519559a
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737176B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes