Sodium Hydroxide → 5-Chloro-2-fluoro-4-methylbenzoic acid

HRID 508422노트

반응식

HRID 508422 반응식
[Cl:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([F:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([F:12])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 58042513Methyl 5-chloro-2-fluoro-4-methylbenzoate

생성물 1

HCID 580424465-Chloro-2-fluoro-4-methylbenzoic acid수율 84%

시약·촉매·용매 1

HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

To a stirred solution of methyl 5-chloro-2-fluoro-4-methylbenzoate (Preparation 12, 340 mg, 1.68 mmol) in dioxane/water (5:1, 12 mL) was added a sodium hydroxide solution (5 M, 1.63 mL, 8.39 mmol). The reaction mixture was stirred at room temperature for 18 hours and then evaporated in vacuo. The resulting residue was suspended in water and extracted with diethyl ether (3×20 mL). The aqueous layer was separated, cooled in an ice bath, acidified with aqueous hydrochloric acid (6 M) and then extracted with EtOAc (30 mL). The combined organics were washed with brine (2×20 mL), dried over sodium sulphate, filtered and evaporated in vacuo to yield the title compound as a white solid (266 mg, 84%).

후처리

  1. customevaporated in vacuo
  2. extractionextracted with diethyl ether (3×20 mL)
  3. customThe aqueous layer was separated
  4. temperaturecooled in an ice bath
  5. extractionextracted with EtOAc (30 mL)
  6. washThe combined organics were washed with brine (2×20 mL)
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-f7de0fe7e88e43f68f8805cfe77bd172
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096500B2

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