Carbon Dioxide → HCID 68868558, compound

HRID 564004Notes

Reaction equation

HRID 564004 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9](Br)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[C:21](=[O:23])=[O:22].O>C1COCC1.CCCCCC.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([C:21]([OH:23])=[O:22])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 67008100HCID 67008100, compoundHCID 178418339Butyllithium

Product 1

HCID 68868558HCID 68868558, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.34 g 3-bromo-4-chlorobenzoic acid tert-butyl ester in 60 ml dry THF were cooled to −78° C. 12.59 ml (1.1 equivalents) of a 1.6 M solution of n-butyl lithium in hexane were added slowly and stirring was continued at −78° C. for 30 min. 20 g solid carbon dioxide were quickly crushed and added to the mixture. Cooling was continued for another 30 min before the mixture was allowed to warm up to room temperature. After 1 hr at room temperature, water and ethyl acetate were added and the organic phase was separated. The water phase was extracted with ethyl acetate and the combined organic phases were evaporated and purified by chromatography on silica in a heptane/ethyl acetate gradient.

Workup

  1. additionadded to the mixture
  2. temperatureCooling
  3. waitwas continued for another 30 min before the mixture
  4. waitAfter 1 hr at room temperature
  5. customthe organic phase was separated
  6. extractionThe water phase was extracted with ethyl acetate
  7. customthe combined organic phases were evaporated
  8. custompurified by chromatography on silica in a heptane/ethyl acetate gradient

Sources & evidence

ORD record
ord-e60448ea53f84db4855df449d7c926ac
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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