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

HRID 41389

Reaction equation

HRID 41389 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-bf2af01711cc46c7809154f7274604a4
Source dataset
uspto-grants-2013_09
Patent number
US08530469B2

Linked notes

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