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

HRID 1182675Notes

Reaction equation

HRID 1182675 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8d0f46c900804d8785f0fd842c6b5a03
Source dataset
uspto-grants-2014_03
Patent number
US08664203B2

Reaction notes

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