[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone → 4-(2-(Benzo[c][1,2,5]thiadiazol-5-yl)-1-(4-(2-chloro-ethoxy)phenyl)but-1-enyl)phenol

HRID 626237Notes

Reaction equation

HRID 626237 reaction equation
[N:1]1[S:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10](=O)[CH2:11][CH3:12])[CH:7]=[CH:6][C:5]=12.[Cl:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=O)=[CH:20][CH:19]=1>>[N:1]1[S:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10]([CH2:11][CH3:12])=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[C:21]3[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH2:15][Cl:14])=[CH:19][CH:20]=3)[CH:7]=[CH:6][C:5]=12

Participants

3

Reactant 2

HCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanoneHCID 896575531-(Benzo[c][1,2,5]thiadiazol-5-yl)propan-1-one

Product 1

HCID 1365028994-(2-(Benzo[c][1,2,5]thiadiazol-5-yl)-1-(4-(2-chloro-ethoxy)phenyl)but-1-enyl)phenolYield 10%

Procedure

According to general procedure of McMurry reaction as example 1, step D described, 1-(benzo[c][1,2,5]thiadiazol-5-yl)propan-1-one (552 mg, 2 mmol) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (384 mg, 2 mmol) to give the desired product (83 mg, 10%, Z/E=1/1).

Workup

  1. customAccording to general procedure of McMurry reaction as example 1, step D

Sources & evidence

ORD record
ord-b3c130df9c824efca71603cc5a4148c8
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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