4-Fluoroaniline → HCID 10686697, compound

HRID 1859749Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][C:14]([F:17])([F:16])[F:15])[C:7]([OH:9])=O)([O-])=O.C(Cl)(=O)C(Cl)=O.[F:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1>>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][C:14]([F:17])([F:16])[F:15])[C:7]([NH:29][C:28]1[CH:30]=[CH:31][C:25]([F:24])=[CH:26][CH:27]=1)=[O:9]

Participants

Reactant 3

HCID 97314-Fluoroaniline

HCID 65578Oxalyl chloride

HCID 186262173-Nitro-4-(trifluoromethoxy)benzoic acid

Product 1

HCID 10686697HCID 10686697, compoundYield 88.5%

Procedure

Prepared according to the procedure described for Example 1 using 3-nitro-4-trifluoromethoxybenzoic acid from Step A (5.1 g, 20.5 mmol), oxalyl chloride (2.1 mL, 20.5 mmol), and 4-fluoroaniline (Aldrich, Milwaukee, Wis.) (4.6 g, 41.1 mmol) to afford the product (5.7 g); m.p. 139-140° C.

Workup

customPrepared

Sources & evidence

ORD record: ord-e040940dff554a77baaffd2d70bd61f5
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528528B2

Reaction notes

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