Carbon tetrabromide → 5-(1-Bromopropyl)-3-methylisoxazole
Reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH:7](O)[CH2:8][CH3:9])[O:4][N:3]=1.C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:12][CH:7]([C:5]1[O:4][N:3]=[C:2]([CH3:1])[CH:6]=1)[CH2:8][CH3:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-(3-methylisoxazol-5-yl)propan-1-ol (0.589 g, 4.17 mmol) in 15 mL of THF was added CBr4 (1.730 g, 5.22 mmol) and triphenylphosphine (1.423 g, 5.42 mmol). The reaction mixture was stirred at room temperature for 3 h. The solid was filtered off, and washed with THF. The filtrate was concentrated and residue was purified by chromatography on silica gel, eluting with 5 to 30% EtOAc/hexane to provide the title compound. Mass Spectrum (ESI) m/z=204.2 (M+1).
Workup
- filtrationThe solid was filtered off
- washwashed with THF
- concentrationThe filtrate was concentrated
- customresidue was purified by chromatography on silica gel
- washeluting with 5 to 30% EtOAc/hexane
Sources & evidence
- ORD record
- ord-86c4d6f88874492c8aeb34b80e129ee1
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296736B2
Reaction notes
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