2,4-Difluoronitrobenzene → (R)-2-(5-fluoro-2-nitrophenylamino)-butyric acid

Reaction equation

F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].FC1C=CC([NH:19][C@H:20]([CH2:24][CH3:25])[C:21]([OH:23])=[O:22])=C([N+]([O-])=O)C=1>>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:19][C@H:20]([CH2:24][CH3:25])[C:21]([OH:23])=[O:22])[CH:7]=1

Participants

Reactant 2

HCID 679672,4-Difluoronitrobenzene

HCID 69223325(R)-2-(4-fluoro-2-nitrophenylamino)-butyric acid

Product 1

HCID 69221394(R)-2-(5-fluoro-2-nitrophenylamino)-butyric acidYield 83%

Procedure

2,4-Difluoronitrobenzene was treated according to the procedure for the preparation of (R)-2-(4-fluoro-2-nitrophenylamino)-butyric acid (see Example 1) to yield (R)-2-(5-fluoro-2-nitrophenylamino)-butyric acid (83%). MS (ESI) m/z 243 ([M#H]+); MS (ESI) m/z 241 ([M−H]−); HRMS: calcd for C10H11FN2O4, 242.07031; found (ESI+), 243.07712.

Sources & evidence

ORD record: ord-cc29205836e0451ca63acdbaa48874b4
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351709B2

Reaction notes

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