Dichloromethane → 5-Bromo-3,3-dimethyl-7-hexanoyl-2,3-dihydrobenzofuran

HRID 2085588Notes

Reaction equation

HRID 2085588 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].ClCCl.[C:8](Cl)(=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[Br:16][C:17]1[CH:18]=[CH:19][C:20]2[O:24][CH2:23][C:22]([CH3:26])([CH3:25])[C:21]=2[CH:27]=1>CCCCCC.C(OCC)(=O)C>[Br:16][C:17]1[CH:18]=[C:19]([C:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:20]2[O:24][CH2:23][C:22]([CH3:25])([CH3:26])[C:21]=2[CH:27]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 67340Hexanoyl chlorideHCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 227312985-Bromo-3,3-dimethyl-7-hexanoyl-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure I and using aluminum chloride 1.76 g, 13.2 mmol), 20 mL of anhydrous dichloromethane, hexanoyl chloride (1.76 g, 13.2 mmol) and 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (Intermediate 2, 1.5 g, 6.61 mmol) followed by flash column chromatography on silica gel (230-400 mesh) using 3% ethyl acetate in hexane as the eluent, the title compound was obtained as a yellow oil. It was used as such for the next step.

Sources & evidence

ORD record
ord-118471512ccd4bb9a9fb8f0c8d4a6837
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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