Water → 9-(Prop-2-en-1-yl)-9H-fluorene-9-carboxylic acid

HRID 2416004Notes

Reaction equation

HRID 2416004 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[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.C(Br)C=C.O>C1COCC1>[CH2:3]([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)[CH:2]=[CH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 748099-CarboxyfluoreneHCID 178418339Butyllithium

Product 1

HCID 142239519-(Prop-2-en-1-yl)-9H-fluorene-9-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

42 ml (0.096 mol) of a 2.5M butyl lithium solution are added dropwise at 0° C. under nitrogen to a solution of 10 g (0.048 mol) of 9-fluorenecarboxylic acid in 150 ml of THF and the mixture is stirred for 30 minutes. Then 4.67 ml (0.054 mol) of allyl bromide are added and the solution is stirred for four hours at ambient temperature. The reaction solution is poured into water and extracted with diethyl ether. The aqueous phase is acidified with 1N hydrochloric acid and extracted with dichloromethane. The organic phase is dried over sodium sulphate and freed from solvent.

Workup

  1. stirringthe solution is stirred for four hours at ambient temperature
  2. extractionextracted with diethyl ether
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulphate

Sources & evidence

ORD record
ord-05d57dc418a0453e920bd7022dfa43b3
Source dataset
uspto-grants-2004_11
Patent number
US06821967B2

Reaction notes

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