Tetrahydrofuran → 5-Bromo-2-phenyl-4-thiazolecarboxylic acid

HRID 1182675ノート

反応式

HRID 1182675 の反応式
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]([OH:14])=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.[Li]CCCC.[Br:25]Br>C1CCCCC1>[Br:25][C:9]1[S:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:11][C:10]=1[C:12]([OH:14])=[O:13]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 24408BromineHCID 1389282-Phenyl-4-carboxythiazoleHCID 178418339Butyllithium

生成物 1

HCID 667697155-Bromo-2-phenyl-4-thiazolecarboxylic acid

試薬・触媒・溶媒 1

HCID 8078Cyclohexane溶媒

実験手順

To a solution of 2-phenyl-1,3-thiazole-4-carboxylic acid (3.2 g) in abs. THF (190 mL) was added at 78° C. over 10 min n-BuLi (25 mL, 1.6M in hexanes). After addition, Br2 (1.3 mL) in cyclohexane (7.4 mL) was added over 10 min. The reaction mixture was allowed to warm up to RT and was stirred at this temperature for 3 h. The reaction mixture was then cooled to 0° C., carefully quenched with HCl (1M, 32 mL) and extracted with EtOAc (2×). The combined org. phases were washed with aq. sodium thiosulfate (20%), dried over MgSO4 and evaporated to dryness to give 4.5 g of the desired product. The crude was used without further purification.

後処理

  1. additionwas added over 10 min
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. customcarefully quenched with HCl (1M, 32 mL)
  4. extractionextracted with EtOAc (2×)
  5. washphases were washed with aq. sodium thiosulfate (20%)
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness

出典と根拠

ORDレコード
ord-8d0f46c900804d8785f0fd842c6b5a03
出典データセット
uspto-grants-2014_03
特許番号
US08664203B2

反応ノート

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