Boron tribromide → HCID 23136380, compound

HRID 1678587Notes

Reaction equation

HRID 1678587 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8]C)[C:5]([F:10])=[CH:4][C:3]=1[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([F:10])=[CH:4][C:3]=1[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 23136325HCID 23136325, compound

Product 1

HCID 23136380HCID 23136380, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl 3-(2,5-difluoro-4-methoxyphenyl)propanoate (1.45 g, 5.9 mmol) was dissolved in dichloromethane (50 mL), a 1 M solution of boron tribromide in dichloromethane (7 mL) was added thereto, and the mixture was stirred at 0° C. for 4 hours. The reaction solution was concentrated under reduced pressure, water was added to the residue, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 70:30) to give the title compound (387 mg, yield 29%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. customThe extract was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 70:30)

Sources & evidence

ORD record
ord-336046a1f46d4c6c8e18a4ac77cd9a5d
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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