2-Bromo-4-nitrophenol → 2-Bromo-1-(difluoromethoxy)-4-nitrobenzene

HRID 1710608Notes

Reaction equation

HRID 1710608 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].Cl[C:13]([F:23])([F:22])C(C1C=CC=CC=1)=O>>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH:13]([F:23])[F:22]

Participants

3

Reactant 2

HCID 221092-Bromo-4-nitrophenolHCID 2382962-Chloro-2,2-difluoroacetophenone

Product 1

HCID 133147042-Bromo-1-(difluoromethoxy)-4-nitrobenzene

Procedure

The compound was prepared starting from commercially available 2-bromo-4-nitrophenol, which was reacted with 2-chloro-2,2-difluoroacetophenone (J. Hu et al., J. Org. Chem., 2006, 71, 9845) to yield 2-bromo-1-difluoromethoxy-4-nitro-benzene. Subsequent Buchwald-Hartwig coupling of 2-bromo-1-difluoromethoxy-4-nitro-benzene with tert.butyloxycarbonyl-piperazine by analogy to preparation example 3.1, reduction of the nitro group to the corresponding aniline by analogy to preparation example 3.2, subsequent coupling with commercially available 2-difluoromethoxybenzene-sulfonylchloride by analogy to preparation example 1.4, and final deprotection under acidic conditions by analogy to example 1 yielded the title compound.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-300dfa31e44440ff94595fdfd52190d2
Source dataset
uspto-grants-2010_09
Patent number
US07790727B2

Reaction notes

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