4-Chloro-3-nitrobenzoic acid → 4-Chloro-3-nitrobenzoyl chloride

HRID 1399421Notes

Reaction equation

HRID 1399421 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].S(Cl)([Cl:16])=[O:15].[CH2:18]([N:20](CC)CC)[CH3:19]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:16])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:20][CH2:18][C:19]([O:8][CH2:6][C:5]1[CH:4]=[CH:3][CH:2]=[CH:10][CH:9]=1)=[O:15]

Participants

5

Reactant 3

HCID 73204-Chloro-3-nitrobenzoic acidHCID 8471TriethylamineHCID 24386Thionyl Chloride

Product 2

HCID 1234774-Chloro-3-nitrobenzoyl chlorideHCID 409140Benzyl glycinate

Procedure

As shown in scheme D, reaction of 4-chloro-3-nitrobenzoic acid with thionyl chloride gave 4-chloro-3-nitrobenzoyl chloride, which on further treatment with benzyl glycinate in presence of triethylamine gave benzyl 2-(4-chloro-3-nitrobenzamido)acetate (intermediate 5). The intermediate 5 is treated either with K18F or K19F in the presence of kryptofix[2.2.2] or 18-crown-6 to yield benzyl 2-(4-fluoro-3-nitrobenzamido)acetate, which on further reduction with hydrogen gas or hydrogen source in the presence of Pd/C gave compound 3.

Sources & evidence

ORD record
ord-862d3b80cb7a4cf1a98b29b65043a910
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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