Triethylamine → Tert-butyl 3,5-difluoro-4-((methylsulfonyloxy)methyl)benzoate

HRID 83889노트

반응식

HRID 83889 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([F:17])[C:14]=1[CH2:15][OH:16])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].CCN(CC)CC.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([F:17])[C:14]=1[CH2:15][O:16][S:26]([CH3:25])(=[O:28])=[O:27])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66740404Tert-butyl 3,5-difluoro-4-(hydroxymethyl)benzoate

생성물 1

HCID 86662220Tert-butyl 3,5-difluoro-4-((methylsulfonyloxy)methyl)benzoate수율 89.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of tert-butyl 3,5-difluoro-4-(hydroxymethyl)benzoate (1.9 g, 7.78 mmol) in DCM was added Et3N (3.27 mL, 23.4 mmol, 3 eq) and methanesulfonylchloride (0.72 mL, 9.3 mmol, 1.2 eq) successively at 0° C. After the reaction was stirred for 30 min, it was extracted with CH2Cl2C and water. Organic layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography (Hex/EtOAc=4:1) to give tert-butyl 3,5-difluoro-4-((methylsulfonyloxy)methyl)benzoate (2.25 g, 89% yield) as a ivory solid.

후처리

  1. extractionit was extracted with CH2Cl2C and water
  2. dry with materialOrganic layer was dried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography (Hex/EtOAc=4:1)

출처 및 근거

ORD 기록
ord-d7c688e7e9ca4161b68862139c9e613c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846739B2

반응 노트

불러오는 중…