Triphenylphosphine → (7-Chloro-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide

HRID 1091781Notes

Reaction equation

HRID 1091781 reaction equation
[Br:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:11])[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>C1COCC1>[Br-:1].[Cl:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:2]([P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[O:3][C:4]2=[O:12]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 20296689HCID 20296689, compound

Product 1

HCID 86633041(7-Chloro-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromideYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-bromo-4-chloroisobenzofuran-1(3H)-one (100) (14 g, 56.57 mmol) and triphenylphosphine (14.84 g, 56.57 mmol) were dissolved THF (200 mL) and heated at reflux for 2 hours. The reaction was cooled and filtered, the filtrate was evaporated to the desired compound as a yellow gum (22.5 g, 78% yield); 1H NMR (400.132 MHz, CDCl3) δ 7.54-7.51 (2H, m), 7.65-7.59 (7H, m), 7.79-7.74 (3H, m), 8.07-8.02 (6H, m), 10.41 (1H, s); m/z (LC-MS, ESI+), RT=2.09 (M+H not detected).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ffad31960d874833b358961c00db63df
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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