Carbon Dioxide → HCID 59214204, compound

HRID 552830Notes

Reaction equation

HRID 552830 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]([CH3:16])[C:12]([F:15])([F:14])[F:13])=[C:6]([CH:9]=1)[C:7]#[N:8].[Li]CCCC.[C:22](=[O:24])=[O:23].[OH-].[Na+]>CCCCCC.C1(C)C=CC=CC=1.C1COCC1>[C:7]([C:6]1[CH:9]=[C:2]([CH:3]=[CH:4][C:5]=1[O:10][CH:11]([CH3:16])[C:12]([F:15])([F:14])[F:13])[C:22]([OH:24])=[O:23])#[N:8]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 59214173HCID 59214173, compoundHCID 178418339Butyllithium

Product 1

HCID 59214204HCID 59214204, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

To 5-bromo-2-(2,2,2-trifluoro-1-methylethoxy)benzonitrile in a mixed solvent of toluene/THF (4:1) was added a solution of n-BuLi in n-hexane at −78° C. With passing a CO2 gas therethrough, the solution was stirred for 0.5 hour. To the reaction solution was added a 1M aqueous NaOH solution to complete the reaction, and followed by extraction with diethyl ether. The organic layer was acidified by adding 1M HCl, extracted with EtOAc, dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel chromatography (chloroform:CH3OH=97:3 to 90:10) to obtain 3-cyano-4-(2,2,2-trifluoro-1-methylethoxy)benzoic acid as a white solid.

Workup

  1. customthe reaction
  2. extractionfollowed by extraction with diethyl ether
  3. additionby adding 1M HCl
  4. extractionextracted with EtOAc
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (chloroform:CH3OH=97:3 to 90:10)

Sources & evidence

ORD record
ord-fdc0c5893b2342ceb84d108484cff9dd
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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