Water → 2,4-Bis-benzyloxy-5-isopropenyl-benzoic acid benzyl ester

HRID 424048Notes

Reaction equation

HRID 424048 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[C:10]1[CH:15]=[C:14](Br)[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][C:11]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.[CH2:41]1[CH2:45]OC[CH2:42]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9](=[O:33])[C:10]1[CH:15]=[C:14]([C:41]([CH3:45])=[CH2:42])[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][C:11]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 46915635Benzyl-2,4-bis-benzyloxy-5-bromobenzoate

Product 1

HCID 592631182,4-Bis-benzyloxy-5-isopropenyl-benzoic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a mixture of 2,4-bis-benzyloxy-5-bromo-benzoic acid benzyl ester (42.9 g, 85.7 mmol), potassium isopropenyl trifluoroborate (14.0 g, 95.2 mmol) and caesium carbonate (83.8 g, 257.1 mmol) in THF (800 mL) was added Pd(PPh3)4 (2.0 g) followed by water (150 mL). The mixture was heated at reflux for 72 h then allowed to cool to ambient. The mixture was reduced in vacuo to remove THF and then partitioned between water (500 mL) and EtOAc (300 mL). The organic portion was washed with brine, dried (MgSO4), filtered and reduced in vacuo to give the title compound (40.9 g) as a brown oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 72 h
  3. temperatureto cool
  4. customto remove THF
  5. custompartitioned between water (500 mL) and EtOAc (300 mL)
  6. washThe organic portion was washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-c57be0d49a9d4149a70e39730c04fe5b
Source dataset
uspto-grants-2012_01
Patent number
US08101648B2

Reaction notes

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