3,3,3-Triethoxyprop-1-yne → 1-Bromo-4-chloro-2-(3,3,3-triethoxyprop-1-ynyl)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1I.[CH2:10]([O:12][C:13]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])[C:14]#[CH:15])[CH3:11]>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:15]#[C:14][C:13]([O:16][CH2:17][CH3:18])([O:12][CH2:10][CH3:11])[O:19][CH2:20][CH3:21]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 23 °C
Procedure
A suspension of 1-bromo-4-chloro-2-iodobenzene (2.5 g, 7.9 mmol), 3,3,3-triethoxyprop-1-yne (2.4 g, 13.9 mmol), copper(I) iodide, (455 mg, 2.3 mmol), and trans-dichlorobis(triphenylphosphine)palladium(II) (559 mg, 0.79 mmol) was treated with ACN (30 mL). The reaction was capped, evacuated under vacuum, backfilled with argon, and treated with TEA (9.9 mL, 71.6 mmol). The reaction was stirred at 23° C. After 2 hours, the reaction mixture was concentrated in vacuo to remove all solvents, diluted with EtOAc (250 mL) and washed with brine (150 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 4% EtOAc/hexane+1% TEA), affording 2.6 g of 1-bromo-4-chloro-2-(3,3,3-triethoxyprop-1-ynyl)benzene.
Workup
- customThe reaction was capped
- customevacuated under vacuum
- concentrationthe reaction mixture was concentrated in vacuo
- customto remove all solvents
- additiondiluted with EtOAc (250 mL)
- washwashed with brine (150 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- custompurified by silica gel chromatography (eluant: 4% EtOAc/hexane+1% TEA)
Sources & evidence
- ORD record
- ord-6aa7c364fdcc41b588f7c6423bb385f6
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635715B2
Reaction notes
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