Carbon Dioxide → 4-(Decyloxy)-3-fluorobenzoic acid

HRID 1289339Notes

Reaction equation

HRID 1289339 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:9]([F:24])[CH:8]=1.[C:25](=[O:27])=[O:26].Cl>C1COCC1.CCOCC>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([C:25]([OH:27])=[O:26])=[CH:8][C:9]=1[F:24])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 146925094-Decyloxy-3-fluorophenyl bromideHCID 178418339Butyllithium

Product 1

HCID 6399744-(Decyloxy)-3-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyllithium was added dropwise to a stirred, cooled (-78° C.) solution of compound of step 2.1 in dry THF. The mixture was maintained under these conditions for 40 mins and then poured into a slurry of dry ether and cardice. The solution was acidified with 36% HCl, washed with water and dried (magnesium sulphate). The solvent was removed to yield a white solid.

Workup

  1. temperatureThe mixture was maintained under these conditions for 40 mins
  2. washwashed with water
  3. dry with materialdried (magnesium sulphate)
  4. customThe solvent was removed
  5. customto yield a white solid

Sources & evidence

ORD record
ord-1090e088da22497eb8bcb2419e46c059
Source dataset
uspto-grants-1998_05
Patent number
US05750050

Reaction notes

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