Carbon Dioxide → 5-Chloro-2-fluoro-4-methylbenzoic acid

HRID 1427906노트

반응식

HRID 1427906 반응식
Br[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][C:3]=1[F:10].C([Mg]Cl)(C)C.[C:16](=[O:18])=[O:17]>C1COCC1>[Cl:8][C:6]1[C:5]([CH3:9])=[CH:4][C:3]([F:10])=[C:2]([CH:7]=1)[C:16]([OH:18])=[O:17]

참가 물질

5

반응물 3

HCID 280Carbon DioxideHCID 27362284-Bromo-2-chloro-5-fluorotolueneHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 580424465-Chloro-2-fluoro-4-methylbenzoic acid수율 49%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-bromo-5-chloro-2-fluoro-4-methylbenzene (11.3 g, 50 mmol) in dry THF (100 mL) was added isopropylmagnesium chloride (30 mL, 2 M) dropwise. After stirring at room temperature for 30 min, dry CO2 was added and the mixture was stirred at room temperature for additional 30 min. The reaction was quenched by sat. NH4Cl and extracted with EtOAc (100 mL×3). The combined organic layers were washed with water (50 mL×3), dried over anhydrous Na2SO4, filtered and concentrated to give the desired product (4.7 g, 49%). LCMS (ESI) m/z: 187.0 [M−H]−.

후처리

  1. stirringthe mixture was stirred at room temperature for additional 30 min
  2. customThe reaction was quenched by sat. NH4Cl
  3. extractionextracted with EtOAc (100 mL×3)
  4. washThe combined organic layers were washed with water (50 mL×3)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c8e479a946ac4461b7c6b48f58814573
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933236B2

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