Benzene → 3-Biphenyl-4-yl-2,5-dihydro-2,5-dimethoxyfuran

HRID 566735Notes

Reaction equation

HRID 566735 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:11]=[CH:10][O:9][CH:8]=2)=[CH:3][CH:2]=1.[C:18]([O-:21])([O-:20])=O.[Na+].[Na+].BrBr.[CH:26]1C=CC=CC=1>CO.CCOC(C)=O>[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:8]([O:9][CH3:10])[O:20][CH:18]([O:21][CH3:26])[CH:11]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 24408BromineHCID 183802933-(Biphenyl-4-yl)furan

Product 1

HCID 183803523-Biphenyl-4-yl-2,5-dihydro-2,5-dimethoxyfuranYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of 3-(biphenyl-4-yl)furan (100 mg, 0.450 mmol) and Na2CO3 (48 mg, 0.45 mmol) in benzene (1 mL) and MeOH (1 mL) at −10° C. was added bromine (22 μL, 0.43 mmol) dropwise via syringe. After 30 minutes at −10° C., the mixture was diluted with EtOAc and filtered twice. The filtrate was concentrated to give a crude solid which was purified via flash column chromatography with a 0-1% EtOAc/CH2Cl2 gradient eluant to provide 90 mg (74%) of a diasteromeric mixture of 3-(biphenyl-4-yl)-2,5-dihydro-2,5-dimethoxyfuran as a colorless oil. 1H NMR (CDCl3): δ 7.70-7.28 (m, 9H), 6.35 (dd, 0.75H, major isomer, J=0.9, 0.9 Hz), 6.30 (d, 0.25H, minor isomer, J=6.0 Hz), 6.04-6.03 (m, 1H, major+minor isomer), 5.71 (d, 0.75H, major isomer, J=0.9 Hz), 3.60-3.40 (m, 6H). Anal. Calculated for C18H18O3: C, 76.57; H, 6.43. Found: C, 76.52; H 6.38.

Workup

  1. filtrationfiltered twice
  2. concentrationThe filtrate was concentrated
  3. customto give a crude solid which
  4. customwas purified via flash column chromatography with a 0-1% EtOAc/CH2Cl2 gradient eluant

Sources & evidence

ORD record
ord-018f762063e54c8c89f682d1469ee1f6
Source dataset
uspto-grants-2001_01
Patent number
US06174915B1

Reaction notes

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