4-Fluorobenzoyl chloride → HCID 86592341, compound

HRID 1269570Notes

Reaction equation

HRID 1269570 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([Br:21])[CH:15]=2)=[C:8]([Cl:22])[C:7]=1[CH2:23][CH3:24])(=[O:4])[CH2:2][CH3:3].[F:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>>[C:1]([O:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:30](=[O:31])[C:29]3[CH:33]=[CH:34][C:26]([F:25])=[CH:27][CH:28]=3)=[C:16]([Br:21])[CH:15]=2)=[C:8]([Cl:22])[C:7]=1[CH2:23][CH3:24])(=[O:4])[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 86592340HCID 86592340, compound

Product 1

HCID 86592341HCID 86592341, compoundYield 89.2%

Procedure

Ethyl(3,5-dichloro-4-[4-amino-3-bromophenoxy]phenyl) propionate (70 mg) was coupled with p-fluorobenzoyl chloride (35 mg), using the method described in Example 1(h). After recrystallization (ethyl acetate/petrolium ether), 80 mg of ethyl(3,5-dichloro-4-[3-bromo-4-p-fluorobenzamidophenoxy]phenyl) propionate was obtained, which was hydrolysed using the method described in Example 1(i). This gave 60 mg of 3,5-dichloro-4-(3-bromo-4-p-fluorobenzamidophenoxy)phenylpropionic acid.

Workup

  1. customAfter recrystallization (ethyl acetate/petrolium ether)

Sources & evidence

ORD record
ord-2bb1ffe0c9cf46ef8f63d8277ec679da
Source dataset
uspto-grants-2007_04
Patent number
US07199265B2

Reaction notes

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