Boron tribromide → HCID 54136541, compound

HRID 569639Notes

Reaction equation

HRID 569639 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13](=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:6]=[CH:7][C:8]=1[O:9]C.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13](=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 54107578HCID 54107578, compound

Product 1

HCID 54136541HCID 54136541, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

In 1 ml of dry dichloromethane was dissolved 128 mg of 1-(3,4-dimethoxyphenyl)-3-oxo-1-octene obtained in the above Example 13-(1), and the solution was cooled at -78° C. Then, 1.5 ml of 1N boron tribromide solution in dichloromethane was added dropwise to the solution, and the temperature was restored to room temperature slowly. Then, the reaction mixture was poured in ice-water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried with magnesium sulfate. The solvent was removed by distillation to give crude product. After recrystallization from water/ethanol, 60 mg of the above caption compound was obtained as crystals.

Workup

  1. customobtained in the above Example 13-(1)
  2. customwas restored to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed by distillation
  7. customto give crude product
  8. customAfter recrystallization from water/ethanol

Sources & evidence

ORD record
ord-a27f6100b3a64d6ea8cef9f645f8ac2d
Source dataset
uspto-grants-1988_03
Patent number
US04733002

Reaction notes

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