Water → 2-Fluorobenzoic acid

HRID 1837802노트

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HRID 1837802 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

HCID 99352-Fluorobenzoic acid

시약·촉매·용매 4

HCID 10271322Benzonitrile;dichloropalladium촉매HCID 3283Diethyl Ether용매HCID 14798Sodium Hydroxide용매HCID 312751,4-Dioxane용매2회

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온도
120 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-642c4b1345614e1e84b5fce92148b5dd
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06784295B2

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