Ethyl 4-bromobenzoate → 4-Bromobenzohydrazide

HRID 1446054Notes

Reaction equation

HRID 1446054 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)C.O.[NH2:14][NH2:15]>CO>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([NH:14][NH2:15])=[O:3])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 22043Ethyl 4-bromobenzoateHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 222194-Bromobenzohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl-4-bromobenzoate is treated with hydrazine monohydrate in methanol under reflux conditions to obtain product X, 4-bromobenzoic hydrazide. Reaction of compound X with bromobenzoic acid in pyridine at 120° C. gives product XI, bis-(4-bromophenyl) hydrazine. Compound XI is then treated with sulfonyl chloride to afford 2,5-bis-(4-bromophenyl)-1,3,4-oxadiazole (Compound XII), which is further reacted 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane under conditions similar to step-3 in Example 1. The resulting product thus obtained is subjected to Suzuki coupling conditions similar to step-5 in Example 1 to obtain the desired product XIII. Other alligator clips which can be introduced are CN, SCN, NH2, pyridine.

Sources & evidence

ORD record
ord-3ca67d99f1c8442dab4b5ca235cc496e
Source dataset
uspto-grants-2010_02
Patent number
US07667043B2

Reaction notes

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