Isobutyryl chloride → HCID 86592336, compound

HRID 1269567Notes

Reaction equation

[C:1]([O:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([Br:27])[CH:21]=2)=[C:14]([Cl:28])[C:13]=1[CH2:29][CH3:30])(=[O:10])[CH:2]=CC1C=CC=CC=1.[C:31](Cl)(=[O:35])[CH:32]([CH3:34])[CH3:33]>>[C:1]([O:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])=[C:22]([Br:27])[CH:21]=2)=[C:14]([Cl:28])[C:13]=1[CH2:29][CH3:30])(=[O:10])[CH3:2]

Participants

Reactant 2

HCID 62325Isobutyryl chloride

HCID 86592337HCID 86592337, compound

Product 1

HCID 86592336HCID 86592336, compoundYield 103.7%

Procedure

Ethyl(3,5-dichloro-4-[4-amino-3-bromophenoxy]phenyl) cinnamate (70 mg) was coupled with isobutyryl chloride (30 mg), using the method described in Example 1(h). After purification on column (silica gel, ethyl acetate/petrolium ether, 1:9), 70 mg of ethyl(3,5-dichloro-4-[3-bromo-4-isobutyramidophenoxy]phenyl) acetate was obtained, which was hydrolysed using the method described in Example 1(i). This gave 50 mg of 3,5-dichloro-4-(3-bromo-4-isobutyramidophenoxy)phenylacetic acid.

Workup

customAfter purification on column (silica gel, ethyl acetate/petrolium ether, 1:9)

Sources & evidence

ORD record: ord-639d9201f53a4ad3ae824af97d1dd28b
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199265B2

Reaction notes

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