Carbon tetrabromide → HCID 59739560, compound
Reaction equation
[C:1]([C:3]1[S:7][N:6]=[C:5]([CH3:8])[C:4]=1[CH2:9]O)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:31]>ClCCl>[Br:31][CH2:9][C:4]1[C:5]([CH3:8])=[N:6][S:7][C:3]=1[C:1]#[N:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
5-Cyano-4-hydroxymethyl-3-methyl-isothiazole (50% purity) (1.14 g, 3.7 mmol) was dissolved in dichloromethane (10 ml) and triphenyl phosphine (1.07 g, 4.0 mmol) and carbon tetrabromide (1.18 g, 3.6 mmol) were added at 0° C. The mixture was stirred at 0° C. for 2 hours, concentrated and the crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane). The colourless oil (0.65 g) consisted of a 1:1 mixture of methyl ester (see Example I14) and product. The mixture was used without further purification.
Workup
- concentrationconcentrated
- customthe crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane)
- customThe mixture was used without further purification
Sources & evidence
- ORD record
- ord-cc2d7e37a4ad4b9f809a1d4660d07db9
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680290B2
Reaction notes
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