Phosphorus oxychloride → HCID 66927046, compound

HRID 81057Notes

Reaction equation

HRID 81057 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:15]=[C:14](O)[C:11]([C:12]#[N:13])=[C:10]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)([Cl:32])=O>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:15]=[C:14]([Cl:32])[C:11]([C:12]#[N:13])=[C:10]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178510509HCID 178510509, compound

Product 1

HCID 66927046HCID 66927046, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 6-(3-bromophenyl)-4-hydroxy-2-(4-phenoxyphenyl)nicotinonitrile (38.8 mg, 0.070 mmol) and phosphoryl trichloride (0.5 mL, 5.38 mmol) was heated to 90° C. for 17 h, then concentrated to give crude 6-(3-bromophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile, which was used in the next reaction without purification. MS (ES+) m/z: 461, 463 (M+H); LC retention time: 4.821 min (analytical HPLC Method A).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-7c9536e3dd27489e9d49321860e10880
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

Loading…