Tetrabutylammonium Fluoride → 1-(3-Bromo-2-methylbenzylidene)-1,3-dihydroisobenzofuran

HRID 1811066Notes

Reaction equation

HRID 1811066 reaction equation
[Br:1][C:2]1[C:3]([CH3:18])=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][OH:17])[CH:5]=[CH:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[C:3]([CH3:18])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH:8]=[C:9]1[C:10]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:16][O:17]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66606721(2-((3-Bromo-2-methylphenyl)ethynyl)phenyl)methanol

Product 1

HCID 666063481-(3-Bromo-2-methylbenzylidene)-1,3-dihydroisobenzofuranYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Step 2 A solution of (2-((3-bromo-2-methylphenyl)ethynyl)phenyl)-methanol (50 mg, 0.166 mmol) and tetrabutylammonium fluoride, 1.0 M in THF (0.332 mL, 0.332 mmol) in THF (0.5 mL) was heated at 67° C. for 2 h. The mixture was diluted with EtOAc, washed twice with water and once with brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from hexane to 80:20 EtOAc-hexane) to provide 1-(3-bromo-2-methylbenzylidene)-1,3-dihydroisobenzofuran as a light yellow solid (36 mg, 72%). 1H NMR (400 MHz, chloroform-d) δ 8.00-8.06 (1H, m), 7.58-7.64 (1H, m), 7.32-7.41 (4H, m), 7.04 (1H, t, J=7.92 Hz), 6.07 (1H, s), 5.49 (2H, s), 2.51 (3H, s). Mass spectrum m/z 301, 303 (M+H)+.

Workup

  1. washwashed twice with water and once with brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (
  5. washeluting with a gradient from hexane to 80:20 EtOAc-hexane)

Sources & evidence

ORD record
ord-85b31e0a716e4154a166b73d91675e57
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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