4-Carboxyphenylboronic Acid → 2'-Methoxy-3'-nitrobiphenyl-3-carboxylic acid

HRID 1710327Notes

Reaction equation

HRID 1710327 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[C:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)([OH:14])=[O:13].[C:24](C1C=CC(B(O)O)=CC=1)(O)=O>>[CH3:24][O:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=[CH:2][C:7]=1[C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([C:12]([OH:14])=[O:13])[CH:20]=1

Participants

4

Reactant 3

HCID 3121834-Carboxyphenylboronic AcidHCID 27339573-Carboxyphenylboronic acidHCID 139704965-Bromo-2-nitrophenol

Product 1

HCID 98567672'-Methoxy-3'-nitrobiphenyl-3-carboxylic acid

Procedure

Following the procedure of Example 1b), except substituting the compound from Example 2b) for 5-bromo-2-nitrophenol and substituting 3-carboxyphenylboronic acid for 4-carboxyphenylboronic acid, the title compound was prepared (2.13 g; 47%) as a tan powder. 1H NMR (300 MHz, d6-DMSO) δ 8.12 (s, 1H), 8.03 (d, J=7.9 Hz, 1H), 7.94 (dd, J=7.9 Hz, 1.5 Hz, 1H), 7.85 (d, J=7.9 Hz, 1H), 7.76 (dd, J=7.5, 1.5 Hz, 1H), 7.66 (t, J=7.5 Hz, 1H), 7.46 (t, j=7.9 Hz, 1H), 3.46 (s, 3H).

Sources & evidence

ORD record
ord-e30053f429914850a4f0c005968d2bac
Source dataset
uspto-grants-2010_09
Patent number
US07790704B2

Reaction notes

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