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

HRID 1091803Notes

Reaction equation

HRID 1091803 reaction equation
[Br:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH3:12])[C:4](=[O:13])[O:3]1.[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[Br-:1].[CH3:12][O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:2]([P+:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[O:3][C:4]2=[O:13]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 109992163-bromo-4-methoxyisobenzofuran-1(3H)-one

Product 1

HCID 11720320(7-Methoxy-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromideYield 53.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-bromo-4-methoxyisobenzofuran-1(3H)-one (122) (3.15 g, 12.96 mmol) and triphenylphosphine (3.40 g, 12.96 mmol) were dissolved THF (50 mL) and heated at reflux over the weekend. The reaction was cooled and filtered to afford the desired material as a white solid (3.50 g, 53.4%); 1H NMR (400.132 MHz, CDCl3) δ 3.42 (3H, s), 7.10 (1H, d), 7.22-7.28 (1H, m), 7.47-7.53 (1H, m), 7.59-7.65 (6H, m), 7.74-7.80 (3H, m), 7.91-8.00 (6H, m), 9.80 (1H, s).

Workup

  1. temperatureheated
  2. temperatureat reflux over the weekend
  3. temperatureThe reaction was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-aac2bedf16314f0d9535b9e773d61741
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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