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2-Bromopropane → 5-Chloro-4-isopropoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29379
Notes
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Reaction equation

HRID 29379 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([OH:17])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH:18](Br)([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][CH:18]([CH3:20])[CH3:19])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 687146975-Chloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687161655-Chloro-4-isopropoxy-3-methyl-benzofuran-2-carboxylic acid ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

To 5-chloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (110 mg) was added 2 mL of isopropylbromide, 150 mg of K2CO3 and 4 mL of DMF. The mixture was stirred at room temperature overnight. The mixture was washed with brine and extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine. Removal of the solvent in vacuo gave 134 mg of 5-chloro-4-isopropoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester as a thick colorless oil (100% yield).

Workup

  1. washThe mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate layers were washed with brine
  4. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-fb5c4bea30e04ce980e57f04c7669630
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07420001B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes