Water → 2,4-Dibromothiazole-5-methanol
Reaction equation
[Br:1][C:2]1[S:3][C:4]([CH:8]=[O:9])=[C:5]([Br:7])[N:6]=1.[BH4-].[Na+].O>CO>[Br:1][C:2]1[S:3][C:4]([CH2:8][OH:9])=[C:5]([Br:7])[N:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 0° C. solution of 2,4-dibromo-1,3-thiazole-5-carbaldehyde (3.38 g, 12.3 mmol) in anhydrous methanol (130 mL) was added sodium borohydride (600 mg, 15.9 mmol). The reaction mixture was stirred at room temperature for 3 hours. Water (100 mL) was added, and the mixture was evaporated. The resultant residue was extracted with EtOAc (3×100 mL). The organic extracts were combined, washed with brine (2×100 mL), dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (2,4-dibromo-1,3-thiazol-5-yl)methanol (2.64 g, 77%). The product was used without further purification.
Workup
- customthe mixture was evaporated
- extractionThe resultant residue was extracted with EtOAc (3×100 mL)
- washwashed with brine (2×100 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
- customdried in vacuo
Sources & evidence
- ORD record
- ord-580c5175d27e4f3eb3d5f4bc120560d2
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040538B2
Reaction notes
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