Methanol → HCID 90118566, compound

HRID 62880Notes

Reaction equation

HRID 62880 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]C)=[C:9]([F:15])[CH:8]=1)C.B(Br)(Br)Br.CO>C(Cl)Cl>[CH3:1][O:3][C:4](=[O:17])[CH:5]([CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([F:15])[CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 901182263-(3-Fluoro-4-methoxy-phenyl)-2-methyl-propionic acid ethyl ester

Product 1

HCID 90118566HCID 90118566, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

After 3-(3-fluoro-4-methoxy-phenyl)-2-methyl-propionic acid ethyl ester (0.728 g, 3.03 mmol) obtained in Step B was dissolved in anhydrous DCM (10 mL), 1M BBr3 solution (4.5 mL, 4.5 mmol) was added thereto at −78° C., and the mixture was stirred at room temperature for 3 hours. After the termination of the reaction, the reactant was added with MeOH, concentrated under reduced pressure, and purified by column chromatography (eluent, EtOAc/Hex=1/2) to obtain the title compound (0.64 g, 99%).

Workup

  1. customAfter the termination of the reaction
  2. concentrationconcentrated under reduced pressure
  3. custompurified by column chromatography (eluent, EtOAc/Hex=1/2)

Sources & evidence

ORD record
ord-127267ae42e844e69480a191b5f2b6b2
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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