3-Fluorophenylboronic acid → Methyl 3-(3-fluorophenyl)-5-methoxybenzoate

HRID 1771670Notes

Reaction equation

HRID 1771670 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1>CO.O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:14][C:15]1[CH:20]=[C:19]([C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 27339863-Fluorophenylboronic acidHCID 15618226Methyl 3-bromo-5-methoxybenzoate

Product 1

HCID 75488445Methyl 3-(3-fluorophenyl)-5-methoxybenzoateYield 88%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of methyl 3-bromo-5-methoxy-benzoate (3.2 g, 13.1 mmol, 1.0 eq), 3-fluorophenylboronic acid (2.0 g, 14.4 mmol, 1.1 eq) K2CO3 (7.2 g, 52.2 mmol, 4.0 eq) and Pd(PPh3)4 (754 mg, 0.65 mmol, 0.05 eq) in a mixture of methanol (10 mL) and dioxane (50 mL) was heated at 70° C. for 4 h under N2. After cooling, the resulting mixture was concentrated and purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:20) to give the title compound as an oil (3.0 g, 88%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe resulting mixture was concentrated
  3. custompurified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:20)

Sources & evidence

ORD record
ord-b2546d3909a749fc9d8c649bf7bf49fc
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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