Carbon tetrabromide → HCID 5363780, compound
Reaction equation
[C:1]([O:4][CH2:5]/[CH:6]=[C:7](\[CH3:16])/[CH2:8]OC1CCCCO1)(=[O:3])[CH3:2].C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:1]([O:4][CH2:5]/[CH:6]=[C:7](\[CH3:16])/[CH2:8][Br:18])(=[O:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 460 mg (2.0 mmol) of (E)-3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-enyl acetate in 20 ml of CH2Cl2 was added a solution of 1.33 g (4 mmol) of CBr4 in 10 ml of CH2Cl2. The solution was cooled to 0° C. and a solution of 1.05 g (4 mmol) of triphenylphosphine was added dropwise. The solution was allowed to warm up to room temperature for 6 hours and stirred at the same temperature for further 1 hour. The precipitate was filtered and the filtrate was evaporated. The residue was purified by chromatography on silica gel using Heptane/EtOAc (8/2) as eluent. 314 mg (1.52 mmol, 76%) of (E)-4-bromo-3-methylbut-2-enyl acetate were isolated as colourless oil.
Workup
- temperatureto warm up to room temperature for 6 hours
- filtrationThe precipitate was filtered
- customthe filtrate was evaporated
- customThe residue was purified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-cf91671d74234cf3a379b212fb201df9
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683045B2
Reaction notes
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