Water → 9-(4-bromobutyl)-9H-fluorene-9-carboxylic acid

HRID 2415137Notes

Reaction equation

HRID 2415137 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH:6]1[C:18]2[CH:17]([C:19]([OH:21])=[O:20])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.[Br:22]C(C)C(Br)C.O>CCCCCC.O1CCCC1>[Br:22][CH2:1][CH2:2][CH2:3][CH2:4][C:17]1([C:19]([OH:21])=[O:20])[C:18]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[C:11]2[C:16]1=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

7

Reactant 4

HCID 962WaterHCID 215082,3-DibromobutaneHCID 748099-CarboxyfluoreneHCID 178418339Butyllithium

Product 1

HCID 107125189-(4-bromobutyl)-9H-fluorene-9-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

89 ml (0.11 mol) of a 1.6 M butyllithium solution in hexane are added dropwise at 0° C. to a solution of 21 g (0.1 mol) of 9-fluorenecarboxylic acid in 700 ml tetrahydrofuran under nitrogen and stirred for one hour. Then, still at 0° C., 13.13 ml (0.11 mol) of dibromobutane are added and the solution is stirred for 30 hours at ambient temperature. After this time, 50 ml of water are added and the mixture is stirred for 30 minutes. The solution is evaporated down, combined with water and extracted with 250 ml of diethyl ether. The aqueous phase is acidified with 150 ml of 1N hydrochloric acid and extracted three times with 250 ml of dichloromethane. The combined organic phases are dried over sodium sulphate and the solvent is removed.

Workup

  1. stirringthe solution is stirred for 30 hours at ambient temperature
  2. stirringthe mixture is stirred for 30 minutes
  3. customThe solution is evaporated down
  4. extractionextracted with 250 ml of diethyl ether
  5. extractionextracted three times with 250 ml of dichloromethane
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. customthe solvent is removed

Sources & evidence

ORD record
ord-b2f6443565714570b0e2f400b7604c05
Source dataset
uspto-grants-2004_11
Patent number
US06818644B1

Reaction notes

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