5'-Fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylic acid → 3'-Chloro-2'-methoxy-4-nitro-2-biphenylcarboxylic acid

HRID 2121787Notes

Reaction equation

HRID 2121787 reaction equation
FC1C=CC(OC)=C(C2C(C(O)=O)=CC([N+]([O-])=O)=CC=2)C=1.[Cl:22][C:23]1[C:24]([O:42][CH3:43])=[C:25]([C:29]2[C:30]([C:38]([O:40]C)=[O:39])=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=2)[CH:26]=[CH:27][CH:28]=1>>[Cl:22][C:23]1[C:24]([O:42][CH3:43])=[C:25]([C:29]2[C:30]([C:38]([OH:40])=[O:39])=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=2)[CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 234336025'-Fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylic acidHCID 54298406Methyl (3'-chloro-2'-methoxy4-nitro-2-biphenylcarboxylate)

Product 1

HCID 234334893'-Chloro-2'-methoxy-4-nitro-2-biphenylcarboxylic acidYield 99%

Procedure

This compound was prepared in a manner similar to that of 5′-fluoro-2′-methoxy-4-nitro-2-biphenylcarboxylic acid (EXAMPLE 107) from methyl (3′-chloro-2′-methoxy-4-nitro-2-biphenylcarboxylate) (230 mg) to afford 0.21 g (99%) of 3′-chloro-2′-methoxy-4-nitro-2-biphenylcarboxylic acid as a white solid. Data for 3′-chloro-2′-methoxy-4-nitro-2-biphenylcarboxylic acid: 1H NMR (400 MHz, acetone-d6) 8.76 (d, J=2.5, 1H), 8.50 (dd, J=8.4, 2.5, 1H), 7.74 (d, J=8.5, 1H), 7.51 (dd, J=7.9, 1.8, 1H), 7.31 (dd, J=7.4, 1.8, 1H), 7.24 (t, J=7.9), 3.47 (s, 3H).

Sources & evidence

ORD record
ord-81b9f046a8554945a5f7d73ad0cd1be2
Source dataset
uspto-grants-2004_02
Patent number
US06696459B1

Reaction notes

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