Diethyl Ether → HCID 11562468, compound

HRID 1060581Notes

Reaction equation

HRID 1060581 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH:21]1[C:29]2[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=2)[C:23](=[O:32])[O:22]1.C(OCC)C>C(#N)C>[Br-:20].[CH3:31][O:30][C:26]1[CH:25]=[C:24]2[C:29](=[CH:28][CH:27]=1)[CH:21]([P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[O:22][C:23]2=[O:32]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 122985403-bromo-6-methoxyisobenzofuran-1(3H)-one

Product 1

HCID 11562468HCID 11562468, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triphenyphosphine (42 g, 0.16 moles) was added to 3-bromo-6-methoxy-3H-isobenzofuran-1-one (41 g, 0.169 moles), obtained as described in example 9, suspended in anhydrous acetonitrile (205 ml) under N2. The mixture was heated under reflux and after 3 hours cooled and concentrated to give a solid which was treated with ethyl ether, filtered and concentrated under vacuum. There were thus obtained 74 g of the title compound (yield: 84%).

Workup

  1. customobtained
  2. temperatureThe mixture was heated
  3. temperatureunder reflux and after 3 hours
  4. temperaturecooled
  5. concentrationconcentrated
  6. customto give a solid which
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c50dbbda56e043fcb8835cc65a707b03
Source dataset
uspto-grants-2003_02
Patent number
US06525055B1

Reaction notes

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