Benzyl Bromide → 5-Benzyloxy-4-t-butylbenzofuran

HRID 2119684Notes

Reaction equation

HRID 2119684 reaction equation
[C:1]([C:5]1[C:10]2[CH:11]=[CH:12][O:13][C:9]=2[CH:8]=[CH:7][C:6]=1[OH:14])([CH3:4])([CH3:3])[CH3:2].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:15]([O:14][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]=[CH:11][C:10]=2[C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 141432464-tert-Butyl-1-benzofuran-5-ol

Product 1

HCID 234428785-Benzyloxy-4-t-butylbenzofuranYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 200 ml of N,N-dimethylformamide were dissolved 40.0 g of 4-t-butyl-5-hydroxybenzofuran [J. Org. Chem. 53, 4135 (1988)], 43.0 g of benzyl bromide and 28.8 g of potassium carbonate, and the mixture was stirred at room temperature for a whole day and night. After N,N-dimethylformamide was distilled off under reduced pressure, the solution was combined with water and extracted with ethyl acetate. The extracted layers were washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 10% ethyl acetate) to give 49.1 g of 5-benzyloxy-4-t-butylbenzofuran as a colorless oil (yield 83%).

Workup

  1. distillationAfter N,N-dimethylformamide was distilled off under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extracted layers were washed with a saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 10% ethyl acetate)

Sources & evidence

ORD record
ord-2e149b78e554412096ac57d7bedd2c35
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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