Water → HCID 66921960, compound

2,6-Dimethyl-4-nitrophenol (5.2 g) and 12.6 g of 1,3-dibromopropane were added to 19 mL of distilled water, the mixture was stirred, and 7.51 g of a 16.6% aqueous sodium hydroxide solution was then added thereto. Further, the mixture was heated under reflux while adding 2.46 g of a 30% aqueous sodium hydroxide solution for 5 hr. The reaction mixture was cooled, and ethyl acetate and brine were added thereto, followed by separation and washing with brine. The ethyl acetate layer was concentrated under the reduced pressure, and the crude product was purified by column chromatography on silica gel (BW300, manufactured by Fuji Sylysia Chemical Ltd., solvent: n-hexane/ethyl acetate) to give 4.97 g of 2-(3-bromopropoxy)-1,3-dimethyl-5-nitrobenzene. Next, 1.0 g of the product, 0.57 g of 4-trifluoromethylphenol, 2 mL of dimethylacetamide, and 0.36 g of potassium carbonate were mixed together, and the mixture was heated at 90 to 100° C. for one hr. The reaction solution was cooled and was then poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a 2% aqueous sodium hydroxide solution and brine and was then concentrated under the reduced pressure to give 1.28 g of 1,3-dimethyl-5-nitro-2-(3-(4-trifluoromethylphenoxy)propoxy)benzene.

1. temperatureFurther, the mixture was heated
2. temperatureunder reflux
3. temperatureThe reaction mixture was cooled
4. customfollowed by separation
5. washwashing with brine
6. concentrationThe ethyl acetate layer was concentrated under the reduced pressure
7. customthe crude product was purified by column chromatography on silica gel (BW300, manufactured by Fuji Sylysia Chemical Ltd., solvent: n-hexane/ethyl acetate)

ORD record

ord-745e35ded16b4ba19f1fcdb65755ddd9

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07880006B2