Triphenylphosphine → (6-Bromo-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide

HRID 1091775Notes

Reaction equation

HRID 1091775 reaction equation
[Br:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Br:11])[CH:9]=2)[C:4](=[O:12])[O:3]1.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1>[Br-:1].[Br:11][C:8]1[CH:9]=[C:10]2[C:5]([C:4](=[O:12])[O:3][CH:2]2[P+:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 577917913,5-dibromoisobenzofuran-1(3H)-one

Product 1

HCID 86633040(6-Bromo-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromideYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-dibromoisobenzofuran-1(3H)-one (94) (6.2 g, 21.24 mmol) and triphenylphosphine (5.57 g, 21.24 mmol) were heated at reflux in tetrahydrofuran (100 mL) overnight. The reaction was cooled and filtered to afford the desired material as a white solid (7.20 g, 71.5% yield); 1H NMR (400.132 MHz, CDCl3) δ 7.23 (1H, s), 7.59 (1H, d), 7.72-7.67 (7H, m), 7.92-7.84 (9H, m), 10.20 (1H, s);

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-53eb79cc48244063a82598b97517d822
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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