4-Methoxyphenol → 3-Chloro-2-p-methoxyphenoxy-5-trifluoromethylpyridine

HRID 1980408Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:13]1[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[Cl:19][C:18]1[C:13]([O:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:14][CH:15]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

p-Methoxyphenol (1.5 g) was added to a suspension of sodium hydride (0.6 g 50% oil dispersion, washed with petroleum) in dry dimethyl sulphoxide (30 ml) and the mixture stirred for 15 minutes. A solution of the combined products (1.5 g) from several preparations carried out as described in paragraph (d), in dimethylsulphoxide (20 ml) was added to the reaction mixture and heated to 60° C. for four hours. A further amount of sodium hydride (0.3 g of 50% oil dispersion, washed with petroleum), and potassium carbonate (1.38 g) was added. Heating was continued for another 4 hours. The mixture was poured into ice and water, and extracted with ether (400 ml). The ether extracts were washed with water, dilute sodium hydroxide, and water, dried, and evaporated to give the product.

Workup

additionwas added to the reaction mixture
temperatureHeating
waitwas continued for another 4 hours
extractionextracted with ether (400 ml)
washThe ether extracts were washed with water, dilute sodium hydroxide, and water
customdried
customevaporated
customto give the product

Sources & evidence

ORD record: ord-689074dc60cc40bfa71a5b6a9a489206
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04508907

Reaction notes

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