HCID 23157235, compound → Methyl 7-bromo-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-carboxylate

HRID 507958Notes

Reaction equation

HRID 507958 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:13][C:14]([CH3:16])=[CH2:15])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[C:11]2[O:12][C:14]([CH3:16])([CH3:15])[CH2:13][C:10]=2[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=1

Participants

4

Reactant 1

HCID 23157235HCID 23157235, compound

Product 1

HCID 23157463Methyl 7-bromo-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-carboxylateYield 74.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-bromo-4-hydroxy-5-(2-methylprop-2-en-1-yl)benzoate (4.1 g, 14.4 mmol) and boron trifluoride diethyl ether complex (2.0 mL, 15.8 mmol) in toluene (30 mL) was stirred at 100° C. for 90 min. After cooling, the reaction solution was diluted with ethyl acetate, washed successively with water, aqueous sodium hydrogencarbonate solution and aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=3:97-15:85) to give the title compound (3.05 g, yield 74%) as colorless prism crystals.

Workup

  1. temperatureAfter cooling
  2. washwashed successively with water, aqueous sodium hydrogencarbonate solution and aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d62c3a22ed1436aa1739e9d1437e9a0
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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