3-Nitrophenylboronic Acid → HCID 23433530, compound

HRID 1939434Notes

Reaction equation

HRID 1939434 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][C:15]=1[CH3:21]>>[NH2:18][C:17]1[CH:19]=[CH:20][C:14]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[C:15]([CH3:21])[CH:16]=1

Participants

3

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 233594-Bromo-3-methylaniline

Product 1

HCID 23433530HCID 23433530, compoundYield 62%

Procedure

This compound was made according to the General Method 14 (EXAMPLE 191) from 3-nitrobenzene boronic acid (673.2 mg, 3.82 mmol) and 4-bromo-3-methylaniline (710.2 mg, 3.82 mmol) to afford 540 mg (62%) of 4-amino-2-methyl-3'-nitrobiphenyl (structure 82 of Scheme XXI, where R1 =R3-5 =R6 =R8 =H, R2 =nitro, R7 =methyl). Data for 4-amino-2-methyl-3'-nitrobiphenyl: 1H NMR (400 MHz, acetone-d6) 8.13 (dd, J=7.5, 1.1, 1H), 8.09 (dd, J=3.9, 1.8, 1H), 7.73 (ddd, J=7.7, 1.6, 1.4, 1H), 7.66 (dd, J=8.0, 7.8, 1H), 6.99 (d, J=8.0, 1H), 6.60 (m, 1H), 4.73 (br s, 1H), 2.18 (s, 3H).

Sources & evidence

ORD record
ord-d73da2ef01a642af93ee009259fcf8d9
Source dataset
uspto-grants-1997_12
Patent number
US05696127

Reaction notes

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