Hydrogen Bromide →

HRID 1060578Notes

Reaction equation

HRID 1060578 reaction equation
[CH:1]([C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])=O.[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Br>C(O)(=O)C.C(#N)C.C(OCC)C>[CH3:13][O:12][C:10]1[CH:11]=[C:3]2[C:4](=[CH:8][C:9]=1[O:14][CH3:15])[C:5](=[O:6])[O:7][CH:1]2[PH2:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 11776TriphenylphosphineHCID 71762072-Formyl-4,5-dimethoxybenzoic acid

Product 0

No Product data yet.

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2-formyl-4,5-dimethoxy-benzoic acid (6.43 g, 30.62 mmoles), obtained as described in example 2, triphenyl-phosphine (8.3 g, 30.62 mmoles), 30% HBr in acetic acid (8.26 ml, 30.62 mmoles) and glacial acetic acid (20 ml) under N2 was heated at 90° C. for 4.5 hours. The mixture was brought to dryness, re-dissolved in acetonitrile (50 ml) and diluted with ethyl ether up to turbidity, then cooled and filtered, and the filtrate was washed with ethyl ether and dried under vacuum to give 13.6 g of the title compound (yield: 83%).

Workup

  1. customobtained
  2. temperaturecooled
  3. filtrationfiltered
  4. washthe filtrate was washed with ethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-cbbf3575b47045bca0481a74c07a90ae
Source dataset
uspto-grants-2003_02
Patent number
US06525055B1

Reaction notes

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