Boron tribromide → HCID 54206997, compound

HRID 1694811Notes

Reaction equation

HRID 1694811 reaction equation
[CH2:1]([C:3]1[CH:10]=[C:9]([O:11]C)[CH:8]=[C:7]([CH2:13][CH3:14])[C:4]=1[CH:5]=[O:6])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:13]([C:7]1[CH:8]=[C:9]([OH:11])[CH:10]=[C:3]([CH2:1][CH3:2])[C:4]=1[CH:5]=[O:6])[CH3:14]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 20083278HCID 20083278, compound

Product 1

HCID 54206997HCID 54206997, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 2.50 g (13.0 mmol) 2,6-diethyl-4-methoxy-benzaldehyde in 15 ml dichloromethane at −60° C. was added dropwise 26.0 ml (26.0 mmol) of a 1 M solution of boron tribromide in dichloromethane. After the addition was complete, the reaction mixture was allowed to warm to room temperature and then heated at reflux for 16 h. The reaction mixture was then cooled to room temperature and poured onto an ice-water mixture. The mixture was diluted with dichloromethane, the phases were separated, and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was resuspended in a 1:1 mixture of ethyl acetate and diethyl ether and extracted with 1 N aqueous sodium hydroxide solution. The phases were separated and the aqueous phase was acidified to pH 1 by addition of concentrated hydrochloric acid and then extracted with ethyl acetate. The phases were separated and the organic phase was washed with saturated brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 1.48 g (64%) of the title compound as a brown crystalline solid. MS (ISP): 177.4 ([M−H]−).

Workup

  1. additionAfter the addition
  2. temperatureheated
  3. temperatureat reflux for 16 h
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. customthe phases were separated
  6. dry with materialthe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionThe residue was resuspended in a 1:1 mixture of ethyl acetate and diethyl ether
  10. extractionextracted with 1 N aqueous sodium hydroxide solution
  11. customThe phases were separated
  12. additionthe aqueous phase was acidified to pH 1 by addition of concentrated hydrochloric acid
  13. extractionextracted with ethyl acetate
  14. customThe phases were separated
  15. washthe organic phase was washed with saturated brine
  16. dry with materialdried over Na2SO4
  17. filtrationfiltered
  18. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0863f47bb6d34f07a734000f65c3fde9
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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