3,4-Dichlorophenol → Dimethyl 5-[(3,4-dichlorophenyl)oxymethyl]isophthalate

HRID 431369Notes

Reaction equation

HRID 431369 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([C:23]([O:25][CH2:26]C)=[O:24])[CH:22]=1)[CH2:18]Br)=[O:14])C>>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:18][C:17]2[CH:16]=[C:15]([C:13]([O:12][CH3:10])=[O:14])[CH:22]=[C:21]([CH:20]=2)[C:23]([O:25][CH3:26])=[O:24])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 72583,4-DichlorophenolHCID 10935954Diethyl 5-(Bromomethyl)isophthalate

Product 1

HCID 18763437Dimethyl 5-[(3,4-dichlorophenyl)oxymethyl]isophthalateYield 90%

Procedure

The title compound was prepared in a manner similar to that described for dimethyl 3-(3,4-dichlorobenzyloxy) isophthalate (Scheme I-A), from 3,4-dichlorophenol and 3,5-bis(ethoxycarbonyl)benzyl bromide. Yield 90%. 1H NMR (CDCl3, 400 MHz), δ8.53 (s, 1H); 8.27 (s, 2H); 7.53 (d, J=8.0 Hz, 2H); 7.38 (s, 1H); 7.08 (d, J=8.0 Hz, 1H); 5.32 (s, 2H); 4.46 (q, J=7.0 Hz, 4H); 1.45 (t, J=7.0 Hz, 6H).

Sources & evidence

ORD record
ord-8efef03c6e724e22a84300e70eb4c24b
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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