4-Bromo-2-fluorobenzonitrile → Methyl 4-bromo-2-fluorobenzimidate

HRID 624621Notes

Reaction equation

HRID 624621 reaction equation
BrC1C=CC2C(=N)NC[CH2:9][O:10]C=2C=1.[Br:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([F:23])[CH:16]=1.C[O-].[Na+]>CO>[Br:14][C:15]1[CH:22]=[CH:21][C:18]([C:19](=[NH:20])[O:10][CH3:9])=[C:17]([F:23])[CH:16]=1

Participants

5

Reactant 3

HCID 7360294-Bromo-2-fluorobenzonitrile2×HCID 10942334Sodium MethoxideHCID 178508525HCID 178508525, compound

Product 1

HCID 71748447Methyl 4-bromo-2-fluorobenzimidate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Scheme 13 shows an alternative synthesis of 8-bromo-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-imine 33 from 4-bromo-2-fluorobenzonitrile 11. Reaction of 11 with sodium methoxide in methanol gives methyl 4-bromo-2-fluorobenzimidate 35. Alkylation of 35 with 2-aminoethanol gives 4-bromo-2-fluoro-N-(2-hydroxyethyl)benzimidamide 36, followed by cyclization to 33.

Sources & evidence

ORD record
ord-81813203f6ec467fa38bf640a06cc216
Source dataset
uspto-grants-2016_04
Patent number
US09303043B2

Reaction notes

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