4-Bromo-3-nitroanisole → HCID 14923755, compound

HRID 1489142Notes

Reaction equation

HRID 1489142 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]>>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[C:14]([N+:21]([O-:23])=[O:22])[CH:15]=1

Participants

3

Reactant 2

HCID 792884-Bromo-3-nitroanisoleHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 14923755HCID 14923755, compoundYield 90%

Procedure

4-Methoxyphenylboronic acid was reacted with 4-bromo-3-nitroanisole as described for 1a to furnish a yellow solid (90% yield): mp 122°-124° C.; [Lund, H. et al, Acta. Chem. Scand., 20, 1631-1644 (1966)]1H NMR (CDCl3) δ7.30 (m, 2H), 7.18 (d, 2H, J=9.0 Hz), 7.10 (d, 1H, J=8.4 Hz), 6.92 (d, 2H, J=9.0 Hz), 3.87 (s, 3H), 3.82 (s, 3H); 13C NMR (CDCl3): δ159.37, 158.80, 149.69, 132.76, 129.43, 129.19, 128.21, 118.60, 114.12, 108.90, 55.89, 55.28. Anal. Calcd for C14H13NO4 : C, 64.86; H, 5.05; N, 5.40. Found: C, 64.77; H, 4.96; N, 5.24.

Sources & evidence

ORD record
ord-ddf7754c39574441b67ea2c74b5e4abc
Source dataset
uspto-grants-1997_10
Patent number
US05677328

Reaction notes

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