Water → 2-Bromo-6-ethenylnaphthalene
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](OS(C(F)(F)F)(=O)=O)[CH:6]=[CH:5]2.[CH:20]([B-](F)(F)F)=[CH2:21].[K+].C(N(CC)CC)C.O>CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:20]=[CH2:21])[CH:8]=2)[CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 45 °C
Procedure
A mixture of trifluoro-methanesulfonic acid 6-bromo-naphthalen-2-yl ester (2) (3.0 g, 8.45 mmol), potassium vinyltrifluoroborate (1.4 g, 11.83 mmol) in EtOH (84 mL) and a 1.0 M aqueous solution of cesium carbonate (17 mL) was purged with nitrogen, to the mixture was added tetrakis(triphenylphosphine)palladium (244 mg, 0.2 mmol) followed by triethylamine (2.3 mL, 17 mmol). The mixture was heated to 45° C. for 16 h under nitrogen and cooled to room temperature. To the mixture was added H2O (84 mL), the resulting suspension was stirred at room temperature for 30 min. and filtered. The wet cake was washed with H2O (30 mL) and dried in the vacuum oven at 45° C. for 16 h to give 1.9 g product. The product is used in the next step without further purification. 1H NMR (400 MHz, CDCl3) d 7.86 (d, 1H), 7.54–7.61 (m, 4H), 7.42–7.44 (dd, 1H), 6.73–6.80 (dd, 1H). 13C NMR (400 MHz, CDCl3) d 136.18, 135.12, 133.77, 131.62, 129.42, 129.32, 129.29, 126.93, 125.84, 124.00, 119.55, 114.54. [M+H]+ at m/z 233.
Workup
- customa 1.0 M aqueous solution of cesium carbonate (17 mL) was purged with nitrogen, to the mixture
- temperaturecooled to room temperature
- filtrationfiltered
- washThe wet cake was washed with H2O (30 mL)
- customdried in the vacuum oven at 45° C. for 16 h
Sources & evidence
- ORD record
- ord-45a75b668dc1468f92b2dac3d4043c07
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07145005B2
Reaction notes
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