Sodium Carbonate → 2'-Fluoro-5-nitro[1,1'-biphenyl]-3-carboxylic acid

HRID 1726385Notes

Reaction equation

HRID 1726385 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.CCO.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.[Pd]>[N+:11]([C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[F:14])[CH:10]=1)[C:5]([OH:7])=[O:6])([O-:13])=[O:12]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2393363-Bromo-5-nitrobenzoic acidHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 463130862'-Fluoro-5-nitro[1,1'-biphenyl]-3-carboxylic acidYield 83%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 3-bromo-5-nitro benzoic acid (1 g, 4.06 mmol) and 2-fluoro-phenyl boronic acid (569 mg, 4.06 mmol) in dimethoxyethane (20 ml) and EtOH (1 ml) was added Na2CO3 (7 ml saturated solution) and palladium tetrakis(triphenylphosphine) (94 mg, 0.08 mmol). The mixture was heated at reflux for 4 h and then stirred at RT for 16 h. The grey precipitate that formed was filtered off and washed with CH2Cl2. The filtrate was evaporated, affording 3-nitro-5-(2-fluorophenyl)benzoic acid (intermediate XXXIVj, 880 mg, 83% yield) as a white solid. M+=262.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 h
  3. customThe grey precipitate that formed
  4. filtrationwas filtered off
  5. washwashed with CH2Cl2
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-5a0d977cf999493185937818ae8e4ded
Source dataset
uspto-grants-2009_02
Patent number
US07491821B2

Reaction notes

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