Pyridine → 2-Bromo-4-(bromomethyl)-5-methyl-1,3-thiazole

HRID 1258551노트

반응식

HRID 1258551 반응식
S(Br)([Br:3])=O.[Br:5][C:6]1[S:7][C:8]([CH3:13])=[C:9]([CH2:11]O)[N:10]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:5][C:6]1[S:7][C:8]([CH3:13])=[C:9]([CH2:11][Br:3])[N:10]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 68176Thionyl bromideHCID 58127549(2-Bromo-5-methylthiazol-4-yl)methanol

생성물 1

HCID 671901442-Bromo-4-(bromomethyl)-5-methyl-1,3-thiazole수율 72%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution thionyl bromide (2.27 g, 10.94 mmol, 1.1 eq.) in 25 ml dry DCM, cooled to 5° C., was added dropwise a solution of (2-bromo-5-methyl-1,3-thiazol-4-yl)methanol (2.07 g, 9.94 mmol, 1 eq.) and pyridine (0.865 g, 10.94 mmol, 1.1 eq.) in 15 ml dry DCM. On complete addition, the cooling bath was removed, the reaction warmed to room temperature and stirred 1.5 hr. 100 ml of water and 100 ml of DCM were added and stirring allowed for 2 mins. The organic layer was separated, dried over MgSO4 and evaporated. The residue was purified by chromatography on silica gel to give 2-bromo-4-(bromomethyl)-5-methyl-1,3-thiazole (1.94 g, 72% yield) as a white solid.

후처리

  1. additionOn complete addition
  2. customthe cooling bath was removed
  3. addition100 ml of water and 100 ml of DCM were added
  4. stirringstirring
  5. waitallowed for 2 mins
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-d64e7b78604e415bb14d565c873d8b19
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466176B2

반응 노트

불러오는 중…