3-Chlorobenzoic Acid → 3-Chloro-3'-methoxybenzophenone
Reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([O:13][CH3:14])[CH:10]=[CH:11][CH:12]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](O)=[O:20]>CCOCC.C1COCC1>[Cl:15][C:16]1[CH:17]=[C:18]([C:19](=[O:20])[C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=2)[CH:22]=[CH:23][CH:24]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -20 °C
Procedure
0.2 mol of butyl-lithium (a suspension in ether, containing 1.8 mol/liter) is placed in a 500 cm3 flask; it is cooled to -20° C. and 37.4 g (0.2 mol) of meta-bromoanisole diluted with 50 cm3 of anhydrous ether are added dropwise; when the addition has ended, the mixture is stirred for 10 to 15 minutes at the same temperature and 15.7 g (0.1 mol) of meta-chlorobenzoic acid dissolved in the minimum amount of THF are added dropwise; the temperature is allowed to return to ambient temperature and the reaction mixture is stirred for 2 hours under these conditions; it is then poured onto water, the ether is decanted and the aqueous phase is extracted with ether; the combined ether phases are washed with sodium bicarbonate and then with water, dried, decolorised and concentrated in vacuo. 26 g of a solid melting at 52° C. are obtained.
Workup
- customis placed in a 500 cm3 flask
- additionare added dropwise
- additionwhen the addition
- additionare added dropwise
- customto return to ambient temperature
- additionit is then poured onto water
- customthe ether is decanted
- extractionthe aqueous phase is extracted with ether
- washthe combined ether phases are washed with sodium bicarbonate
- dry with materialwith water, dried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-e92438441c43435ab0c1da5b2ecb205c
- Source dataset
- uspto-grants-1981_09
- Patent number
- US04287209
Reaction notes
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