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Carbonate Ion → 1-(5-Bromo-3-methyl-1-benzofuran-2-yl)-2-methylpropan-1-one

HRID 2091385
Notes
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Reaction equation

HRID 2091385 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.[C:12](=O)([O-])[O-].BrC[C:18](=[O:22])[CH:19]([CH3:21])[CH3:20].[K]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:9]([C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])=[C:8]([CH3:12])[C:6]=2[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 19660Carbonate IonHCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 5462222PotassiumHCID 108990371-Bromo-3-methylbutan-2-one

Product 1

HCID 290760271-(5-Bromo-3-methyl-1-benzofuran-2-yl)-2-methylpropan-1-oneYield 92.9%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

1-[5-Bromo-2-hydroxyphenyl]ethanone (8.4 g) was dissolved in N,N-dimethylformamide (50 mL). To the reaction mixture were added carbonate (16.2 g) and 1-bromo-3-methylbutan-2-one (8.4 g) synthesized in Example A75(1) at room temperature potassium, and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was filtered through celite, water (100 mL) was added, and the mixture was extracted with diethyl ether (50 mL×2). The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The precipitate was washed with diisopropyl ether to give the title object compound (10.2 g, 77%) as a pale-yellow solid.

Workup

  1. customsynthesized in Example A75(1) at room temperature
  2. filtrationThe reaction mixture was filtered through celite, water (100 mL)
  3. additionwas added
  4. extractionthe mixture was extracted with diethyl ether (50 mL×2)
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe precipitate was washed with diisopropyl ether

Sources & evidence

ORD record
ord-fe3c74d81ec04a649bc7f08fb37a7082
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08436043B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes