Boron tribromide → HCID 54206997, compound

HRID 254589Notes

Reaction equation

HRID 254589 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 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 9.00 g (46.8 mmol)) 2,6-diethyl-4-methoxy-benzaldehyde in 50 ml dichloromethane at −78° C. was added 103 ml (103 mmol) of a 1 M solution of boron tribromide in dichloromethane and the reaction mixture was allowed to warm to room temperature and then heated at reflux for 16 h. The reaction mixture was quenched by pouring onto ice and the resulting mixture was then diluted with ethyl acetate and washed sequentially with water and with saturated brine. The phases were separated and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo to afford 8.68 g (100%) of the title compound as a brown crystalline solid. MS (ISP): 177.4 ([M-H]−, 100%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. customThe reaction mixture was quenched
  4. additionby pouring onto ice
  5. additionthe resulting mixture was then diluted with ethyl acetate
  6. washwashed sequentially with water and with saturated brine
  7. customThe phases were separated
  8. dry with materialthe organic phase was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d3137fd71e449ca91d940dad54008b0
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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