Hydrochloric Acid → 4-(4-Fluorophenyl)benzoic acid

HRID 1984944Notes

Reaction equation

HRID 1984944 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.Cl>C1COCC1.[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.CCCCCC.C(O)C>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 114644-Bromobenzoic acidHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 27826894-(4-Fluorophenyl)benzoic acidYield 82%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4-bromobenzoic acid (5 g, 0.025 mol) in THF (150 mL) under an atmosphere of argon were added tetrakis(triphenylphosphine) palladium(0) (862 mg, 0.75 mmol), 2 M aqueous Na2CO3 (30 mL), and a solution 4-fluorophenyboronic acid (3.48 g, 0.025 mol) in a minimal amount of ethanol (˜10 mL). The resulting reaction mixture was stirred at reflux under an argon atmosphere for overnight. The reaction mixture was cooled to ambient temperature and acidified with addition of 1 M HCl aqueous. The aqueous layer was extracted with Et2O (three times). The organic layers were combined, dried over MgSO4, filtered and concentrated. The resulting precipitate was crystallized in Et2O and hexane to give 4′-fluoro-biphenyl-4-carboxylic acid (4.4 g, 0.020 mol, 82%) as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. temperatureat reflux under an argon atmosphere for overnight
  3. extractionThe aqueous layer was extracted with Et2O (three times)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting precipitate was crystallized in Et2O

Sources & evidence

ORD record
ord-bdd5b86ae85d4d9f965cc90760961aba
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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