Carbon Dioxide → HCID 66901561, compound
Reaction equation
I[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[CH:4][C:3]=1[O:19][CH3:20].C([Li])CCC.[C:26](=[O:28])=[O:27]>C1COCC1>[CH3:20][O:19][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:6]=[C:7]([CH3:8])[C:2]=1[C:26]([OH:28])=[O:27]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 7.70 g (19.6 mmol) of 4-iodo-3-methoxy-5-methyl-3′-trifluoromethyl-biphenyl in 190 ml of THF was cooled down to −75° C.; then, 13.5 ml (21.6 mmol) of an n-butyl lithium solution (1.6 molar in n-hexane) was added slowly below −70° C. One hour later, the dark-brown reaction mixture was treated with an excess of carbon dioxide gas (dried by bubbling through H2SO4 conc. in a gas washing device) during 2 hours and then warmed up to 0° C. It was subsequently poured into crashed ice, the pH was then adjusted to 3-4 with HCl/H2O (1N) and the mixture was extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by re-crystallization from EtOAc/heptane to give 2.90 g (48%) of the title compound as colorless solid. MS: 309.3 (M−H−).
Workup
- customdried
- customby bubbling through H2SO4 conc. in a gas
- washwashing device) during 2 hours
- additionIt was subsequently poured
- extractionthe mixture was extracted twice with EtOAc
- washthe organic phases were washed with water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe residue was purified by re-crystallization from EtOAc/heptane
Sources & evidence
- ORD record
- ord-25e061a8450a4e03a614438fc5bbed8c
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153805B2
Reaction notes
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