Toluene → HCID 70872198, compound

HRID 1918343Notes

Reaction equation

HRID 1918343 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6](Br)[CH:5]=1.[F:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].C(=O)(O)[O-].[Na+].C1(C)C=CC=CC=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:17]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:15]([F:14])[CH:16]=2)[C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)=[O:13]

Participants

7

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 611662Methyl 3-bromo-4-methoxybenzoateHCID 27821943-Fluoro-4-methoxyphenylboronic acid

Product 1

HCID 70872198HCID 70872198, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

3-Bromo-4-methoxybenzoic acid methyl ester (500 mg, 2.04 mmol), 3-fluoro-4-methoxyphenylboronic acid (381 mg, 2.24 mmol), Tetrakis(triphenylphosphine)-palladium(0) (117 mmol, 0.10 mmol), and sodium bicarbonate (514 mg, 6.12 mmol) were partitioned between toluene (5 ml) and water (5 ml) and stirred in reflux for 36 hours. The mixture was partitioned between ethyl acetate and water, the combined organic extracts were dried over sodium sulfate and evaporated to dryness. The raw material was purified by silica gel chromatography with a heptane/ethyl acetate gradient. to yield the title compound (500 mg).

Workup

  1. temperaturein reflux for 36 hours
  2. customThe mixture was partitioned between ethyl acetate and water
  3. dry with materialthe combined organic extracts were dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe raw material was purified by silica gel chromatography with a heptane/ethyl acetate gradient

Sources & evidence

ORD record
ord-bedf59f0cae846b59c6e880777fcd761
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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