Benzene, 1-(bromomethyl)-3-nitro- → 3-(4-Cyanophenoxy)-5-(3-nitrobenzyloxy)benzoic acid ethyl ester

HRID 1024748Notes

Reaction equation

HRID 1024748 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[CH:6]=1)[CH3:2].Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=1>>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9]([O:11][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=2)[CH:8]=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[CH:6]=1)[CH3:2]

Participants

3

Reactant 2

HCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 668184083-(4-Cyanophenoxy)-5-hydroxy benzoic acid ethyl ester

Product 1

HCID 668185913-(4-Cyanophenoxy)-5-(3-nitrobenzyloxy)benzoic acid ethyl esterYield 80.8%

Procedure

Using 1.2 g (4.23 mmol) of 3-(4-cyano phenoxy)-5-hydroxy benzoic acid ethyl ester and 1-bromomethyl-3-nitro-benzene (0.913 g, 4.23 mmol) and following the procedure of Example 42(b) afforded 1.43 g of the required product. 1H NMR (DMSO-d6): δ 1.3 (3H, t), 4.3 (2H, q), 5.4 (2H, s), 7.2 (4H, m), 7.45 (1H, s), 7.72 (1H, t), 7.9 (3H, m), 8.25 (1H, d), 8.35 (1H, s).

Sources & evidence

ORD record
ord-fe9c3f5a8e4043a6af1c61a1988cdcca
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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