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

HRID 1625319Notes

Reaction equation

HRID 1625319 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.[CH2:34](N)[CH2:35][CH2:36]C>CC(O)C.O.O>[CH2:1]([O:8][C:9](=[O:33])[C:10]1[CH:15]=[C:14]([C:35]([CH3:36])=[CH2:34])[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

5

Reactant 2

HCID 8007ButylamineHCID 46915635Benzyl-2,4-bis-benzyloxy-5-bromobenzoate

Product 1

HCID 592631182,4-Bis-benzyloxy-5-isopropenyl-benzoic acid benzyl esterYield 119.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

A mixture of 2,4-bis-benzyloxy-5-bromo-benzoic acid benzyl ester (10.0 g, 20 mmol), potassium isopropenyl trifluoroborate (4.0 g, 27.2 mmol) and n-butylamine (6.0 mL, 60 mmol) in 2-propanol/water (2:1, 200 mL) was purged with N2 for 5 minutes. To this mixture was added [1,1′-bis(diphenyl-phosphino)ferrocene]dichloropalladium(II) (816 mg, 1.09 mmol) and the mixture was heated at reflux for 20 h. The mixture was allowed to cool to ambient then diluted with water (400 mL) and extracted with EtOAc (2×300 mL). The combined organic extracts were washed with 1M aqueous HCl, brine, dried (MgSO4), filtered through a plug of Celite and the filtrate reduced in vacuo to give the title compound (11.1 g) as a brown gum.

Workup

  1. customwas purged with N2 for 5 minutes
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 20 h
  4. temperatureto cool
  5. extractionextracted with EtOAc (2×300 mL)
  6. washThe combined organic extracts were washed with 1M aqueous HCl, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered through a plug of Celite

Sources & evidence

ORD record
ord-20d6ffe11ae943dabb9f597778bbc515
Source dataset
uspto-grants-2014_07
Patent number
US08779132B2

Reaction notes

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