Boron tribromide → 4-(3-(4-Hydroxyphenyl)-5,5-dimethyl-4-oxo-4,5-dihydro furan-2-yl)benzonitrile

HRID 1798686Notes

Reaction equation

HRID 1798686 reaction equation
B(Br)(Br)Br.C([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:23](=[O:24])[C:22]([CH3:26])([CH3:25])[O:21][C:20]=2[C:27]2[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=2)=[CH:15][CH:14]=1)C1C=CC=CC=1>C(Cl)Cl>[OH:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[C:23](=[O:24])[C:22]([CH3:25])([CH3:26])[O:21][C:20]=2[C:27]2[CH:28]=[CH:29][C:30]([C:31]#[N:32])=[CH:33][CH:34]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 666439234-(3-(4-(Benzyloxy)phenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile

Product 1

HCID 666438444-(3-(4-Hydroxyphenyl)-5,5-dimethyl-4-oxo-4,5-dihydro furan-2-yl)benzonitrileYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (3.4 g, 15.8 mmol) was added to a solution of 4-(3-(4-(benzyloxy)phenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile (2.5 g, 6.3 mmol) in DCM at 0° C. & the mixture was stirred for 1 h (reaction was monitored by TLC). Upon complete consumption of the starting material, the mixture was quenched with chilled water and extracted with DCM. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to afford 4-(3-(4-hydroxyphenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile (1.8 g, 93.2%) as yellow solid. 1H NMR: 500 MHz, CDCl3: δ 9.6 (s, 1H), 7.95 (d, 2H), 7.75 (d, 2H), 7.0 (d, 2H), 6.75 (d, 2H), 1.5 (s, 6H).

Workup

  1. custom(reaction was monitored by TLC)
  2. customUpon complete consumption of the starting material
  3. customthe mixture was quenched with chilled water
  4. extractionextracted with DCM
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-901bb9077d214182a12e4d2c2f286abd
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

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