2-Bromothiazole → Methyl 3-bromo-5-(hydroxy(thiazol-2-yl)methyl)benzoate

HRID 1845297Notes

Reaction equation

HRID 1845297 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Mg]Cl)(C)C.[Br:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([CH:23]=[O:24])[CH:22]=1)[C:16]([O:18][CH3:19])=[O:17]>C1COCC1>[Br:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([CH:23]([OH:24])[C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[CH:22]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 764302-BromothiazoleHCID 11436457Methyl 3-bromo-5-formylbenzoateHCID 178418918HCID 178418918, compound

Product 1

HCID 58187949Methyl 3-bromo-5-(hydroxy(thiazol-2-yl)methyl)benzoateYield 66.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-bromothiazole (0.40 g, 24.4 mmol) in THF (60 mL) under nitrogen at rt was added 2M isopropylmagnesium chloride solution in THF (10 mL, 20 mmol). The mixture was stirred at rt for 1 h and then cooled to 0° C. Methyl 3-bromo-5-formylbenzoate (1.0 g, 4.1 mmol) was added and the reaction mixture was stirred at 0° C. for 30 minutes. The reaction mixture was quenched with water (30 mL) and extracted with CH2Cl2 (60 mL×3). The combined organic layers were dried over anhydrous MgSO4 and concentrated. The residue was purified by flash chromatography to afford the title compound (0.90 g).

Workup

  1. temperaturecooled to 0° C
  2. stirringthe reaction mixture was stirred at 0° C. for 30 minutes
  3. customThe reaction mixture was quenched with water (30 mL)
  4. extractionextracted with CH2Cl2 (60 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-517759d965144f37b04399b9fd6cf0fb
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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