4-Methyl-5-(2-hydroxyethyl)thiazole → 5-(2-bromoethyl)-4-methylthiazole
Reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][CH2:8]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:29]N1C(=O)CCC1=O>ClCCl>[Br:29][CH2:8][CH2:7][C:6]1[S:5][CH:4]=[N:3][C:2]=1[CH3:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
1 g (6.98 mmol) of 2-(4-methylthiazol-5-yl)ethanol is dissolved in 15 mL of dichloromethane. The solution is cooled to 0° C. When the temperature is reached, 1.85 g (6.98 mmol) of triphenylphosphine are added, followed by portionwise addition of 1.30 g (6.98 mmol) of N-bromosuccinimide. After stirring for 2 hours at 0° C., the mixture is evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 50/50 EtOAc/heptane) to give 900 mg of 5-(2-bromoethyl)-4-methylthiazole, the characteristics of which are as follows:
Workup
- customthe mixture is evaporated to dryness
- customThe residue is purified by chromatography on silica gel (eluent: 50/50 EtOAc/heptane)
Sources & evidence
- ORD record
- ord-d1814a2221f348e489e0a298cd611760
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321790B2
Reaction notes
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