Water → 2-Fluorobenzoic acid

HRID 1837802Notes

Reaction equation

HRID 1837802 reaction equation
[C:1](=[O:4])([O-])[O-:2].[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[F:14].O.C12(PC34CC(CC3)CC4)CC(CC1)CC2>O1CCOCC1.[OH-].[Na+].C(OCC)C.[Cl-].[Cl-].C(#N)C1C=CC=CC=1.C(#N)C1C=CC=CC=1.[Pd+2]>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:1]([OH:2])=[O:4]

Participants

9

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 612591-Bromo-2-fluorobenzeneHCID 22679109HCID 22679109, compound

Product 1

HCID 99352-Fluorobenzoic acid

Reagents, catalysts & solvents 4

HCID 10271322Benzonitrile;dichloropalladiumCatalystHCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
120 °C

Procedure

Sodium carbonat (3.34 g, 32 mmols), 1-bromo-2-fluorobenzene (3.68 g, 21 mmols), water (1.1 g, 63 mmol) and 40 ml of dioxane are placed in a glass autoclave. The autoclave is rinsed with nitrogen and heated to 120° C. A solution of palladium bis(benzonitrile) dichloride (161 mg, 0.42 mmols) and dinorbornylphosphine (420 mg, 1.90 mmols) in 2 ml of dioxane (prepared under argon) is added, and then 6 bars CO are applied. After 16 hours at 135° C., the mixture is allowed to cool. The reaction mixture is taken up in sodium hydroxide solution and diethyl ether. The aqueous phase is separated and acidified with concentrated hydrochloric acid. The title compound precipitates in the form of colourless crystals. Yield of title compound: 1.6 g (54%).

Workup

  1. washThe autoclave is rinsed with nitrogen
  2. temperatureto cool
  3. customThe aqueous phase is separated
  4. customThe title compound precipitates in the form of colourless crystals

Sources & evidence

ORD record
ord-642c4b1345614e1e84b5fce92148b5dd
Source dataset
uspto-grants-2004_08
Patent number
US06784295B2

Reaction notes

Loading…