Phosphorus tribromide → HCID 67331259, compound
Reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([CH3:15])[C:4]=1[CH2:16][CH:17]=[C:18]([CH3:26])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:25])[CH2:23]O.P(Br)(Br)[Br:28]>C1COCC1>[Br:28][CH2:23][C:22]([CH3:25])=[CH:21][CH2:20][CH2:19][C:18]([CH3:26])=[CH:17][CH2:16][C:4]1[C:5]([CH3:15])=[C:6]([O:13][CH3:14])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[O:2][CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
6.45 g (18.22 mmol) of 8-(1,4-dimethoxy-3-methyl-naphtalen-2-yl)-2,6-dimethyl-octa-2,6-dien-1-ol was dissolved in 45 ml of dry THF. At 0° C., 0.9 ml (2.59 g, 9.58 mmol) PBr3 was added drop wise via septum and syringe and the clear, colourless solution was stirred at 0° C. for 3 h. The reaction was quenched by addition of ice cold water. The layers were separated and the aqueous layer was extracted with ether. The combined organic extracts were washed with NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo to give 2-(8-bromo-3,7-dimethyl-octa-2,6-dienyl)-1,4-dimethoxy-3-methyl-naphtalene as a colorless oil (6.29 g, 15.08 mmol, 83%). The crude product was used for the next step without further purification.
Workup
- customThe reaction was quenched by addition of ice cold water
- customThe layers were separated
- extractionthe aqueous layer was extracted with ether
- washThe combined organic extracts were washed with NaHCO3 and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c2261ec2c50a43bf903953d0551acb32
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012693B2
Reaction notes
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