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

HRID 1258551ノート

反応式

HRID 1258551 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d64e7b78604e415bb14d565c873d8b19
出典データセット
uspto-grants-2013_06
特許番号
US08466176B2

反応ノート

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