4-(Bromomethyl)benzonitrile → 3-(4-Cyanobenzyloxy)-5-(4-cyanophenoxy)benzoic acid ethyl ester

HRID 1024732Notes

Reaction equation

HRID 1024732 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].[C:22]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1)#[N:23]>>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:6]=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[CH:8]=[C:9]([O:11][CH2:28][C:27]2[CH:30]=[CH:31][C:24]([C:22]#[N:23])=[CH:25][CH:26]=2)[CH:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 668184083-(4-Cyanophenoxy)-5-hydroxy benzoic acid ethyl ester

Product 1

HCID 668186513-(4-Cyanobenzyloxy)-5-(4-cyanophenoxy)benzoic acid ethyl esterYield 78.6%

Procedure

Using 0.66 g (2.3 mmol) of 3-(4-cyano phenoxy)-5-hydroxy benzoic acid ethyl ester and 4-cyanobenzylbromide (0.45 g, 2.3 mmol) and following the procedure of Example 42(b) afforded 0.72 g of the required product. 1H NMR (DMSO-d6): δ 1.3 (3H, t), 4.3 (2H, q), 5.35 (2H, s), 7.16 (4H, m), 7.44 (1H, s), 7.66 (2H, s), 7.88 (4H, d).

Sources & evidence

ORD record
ord-ead070ac2bb5420083410719f5e6552a
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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