1,2-Dibromoethane → 2-[2,6-Dichloro-4-(2,2,2-trifluoroethylthio)-phenoxy]-ethyl bromide

HRID 64648Notes

Reaction equation

[Na].[Cl:2][C:3]1[CH:8]=[C:7]([S:9][CH2:10][C:11]([F:14])([F:13])[F:12])[CH:6]=[C:5]([Cl:15])[C:4]=1[OH:16].[CH2:17](Br)[CH2:18][Br:19]>C(O)C>[Cl:15][C:5]1[CH:6]=[C:7]([S:9][CH2:10][C:11]([F:13])([F:14])[F:12])[CH:8]=[C:3]([Cl:2])[C:4]=1[O:16][CH2:17][CH2:18][Br:19]

Participants

Conditions

Temperature: 40 °C

Procedure

To an ethanol solution of sodium ethylate obtained by dissolving 0.7 g of metallic sodium in 50 ml of ethanol were added 8.9 g of 2,6-dichloro-4-(2,2,2-trifluoroethylthio)-phenol and 20 g of ethylene bromide. The mixture was stirred at 40° C. for 2 hours and under reflux for 4 hours. Ethanol and the excess of ethylene bromide were evaporated. The residue was taken into 150 ml of toluene, washed with a 5% aqueous solution of potassium hydroxide and water in this sequence, and dried over anhydrous sodium sulfate. Toluene was evaporated, and the residue was distilled under reduced pressure to give 7.2 g of 2-[2,6-dichloro-4-(2,2,2-trifluoroethylthio)-phenoxy]-ethyl bromide with the b.p.=124°-126° C./0.8 mmHg.

Workup

temperatureunder reflux for 4 hours
customEthanol and the excess of ethylene bromide were evaporated
washwashed with a 5% aqueous solution of potassium hydroxide and water in this sequence
dry with materialdried over anhydrous sodium sulfate
customToluene was evaporated
distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record: ord-ea7863179ebd4bd8baa5658f7a499e8f
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04609669

Reaction notes

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