Iodine → 4-Chloro-2-fluoro-6-iodobenzoic acid

HRID 596054

반응식

HRID 596054 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.C(O)(=O)C.C(O)(=O)C.[I:20]C1C=CC=CC=1.II.CN(C=O)C>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:10]=[C:9]([I:20])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1

참가 물질

7

반응물 4

HCID 807IodineHCID 6228DimethylformamideHCID 991524-Chloro-2-fluorobenzoic acid2회HCID 12217721Iodo benzene diacetate

생성물 1

HCID 1180459354-Chloro-2-fluoro-6-iodobenzoic acid

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To a 250 mL flask were added 4-chloro-2-fluorobenzoic acid (4 g, 22.92 mmol), Pd(OAc)2 (0.257 g, 1.146 mmol), iodobenzene diacetate (8.12 g, 25.2 mmol), iodine (6.40 g, 25.2 mmol) and DMF (60 mL). The solution was heated under a nitrogen atmosphere at 100° C. for 20 h. LCMS showed about half of 4-chloro-2-fluorobenzoic acid was converted to the product (LCMS retention time 0.98 min, no MH+ peak). After cooling to room temperature, the solution was diluted with EtOAc and washed three times with 1 N HCl. The aqueous layers were combined and extracted once with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated to give a dark brown oil (16.4 g, 42% pure), which was taken to the next step without purification.

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed three times with 1 N HCl
  3. extractionextracted once with EtOAc
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a dark brown oil (16.4 g, 42% pure), which
  7. customwas taken to the next step without purification

출처 및 근거

ORD 기록
ord-3f19965fe351414d9c0e744a7d758022
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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