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

HRID 1900490Notes

Reaction equation

HRID 1900490 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 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-tert-butyl-5-hydroxybenzofuran [J. Org. Chem., 53, 4135 (1988); 40 g, 0.21 mol], benzyl bromide (43 g, 0.25 mol) and potassium carbonate (28.8 g, 0.21 mol) were dissolved in N,N-dimethylformamide (200 ml) and the solution was stirred at room temperature for 24 h. After distilling off the N,N-dimethylformamide under vacuum, water was added to the residue and the mixture was subjected to extraction with ethyl acetate. The extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 5-benzyloxy-4-tert-butylbenzofuran [49.1 g (yield, 83%)]. Mass 280(M+), 224, 189, 161, 91

Workup

  1. distillationAfter distilling off the N,N-dimethylformamide under vacuum, water
  2. additionwas added to the residue
  3. extractionthe mixture was subjected to extraction with ethyl acetate
  4. washThe extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-2e5d7954a0e34f51b9f06816daeb4625
Source dataset
uspto-grants-1996_11
Patent number
US05574178

Reaction notes

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