Boron tribromide → HCID 18624168, compound

HRID 1860689Notes

Reaction equation

HRID 1860689 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([CH3:19])([CH3:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([CH3:18])([CH3:19])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18624146HCID 18624146, compound

Product 1

HCID 18624168HCID 18624168, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl 4-(2-bromo-4-methoxyphenyl)-3,3-dimethylbutanoate (4.5 g, 13.7 mmoles) was dissolved in methylene chloride (60 mL) and was cooled to 0° C. and 1M boron tribromide in methylene chloride (27.0 mL) was added. The mixture was stirred at 0° C. for one hour under nitrogen atmosphere. The reaction mixture was quenched with ethanol (60.0 mL) and was warmed to room temperature and was stirred at room temperature for 1 hour. The solvents were removed under reduced pressure and residue was dissolved in ethyl acetate and was washed with a saturated solution of sodium bicarbonate and water, dried (Na2SO4) and concentrated to yield 4.0 g (93%) of desired product. NMR spectrum of the product was consistent for the proposed structure.

Workup

  1. customThe reaction mixture was quenched with ethanol (60.0 mL)
  2. temperaturewas warmed to room temperature
  3. stirringwas stirred at room temperature for 1 hour
  4. customThe solvents were removed under reduced pressure and residue
  5. dissolutionwas dissolved in ethyl acetate
  6. washwas washed with a saturated solution of sodium bicarbonate and water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8e94f4b6452247f398589c799bf78d4d
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

Loading…