Sodium hydride → 2-(2-Methylthioethoxy)nitrobenzene

HRID 4241

Reaction equation

[OH:1][CH2:2][CH2:3][S:4][CH3:5].[H-].[Na+].F[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16]>O1CCCC1>[CH3:5][S:4][CH2:3][CH2:2][O:1][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16]

Participants

Conditions

Temperature: 40 °C

Procedure

16.3 g of 2-hydroxyethylmethyl sulfide are added dropwise at 20°-25° C. to 8.5 g of a 55% NaH suspension in 150 ml of absolute tetrahydrofuran. The mixture is stirred for 1 hour at 20° C. and for 20 minutes at 40° C., and 25 g of 1-fluoro-2-nitrobenzene are subsequently added at 20° C. After the suspension has been stirred for 10 hours at 20° C., the tetrahydrofuran is distilled off in vacuo. Water is added to the residue, and extraction is repeatedly performed with ether. There is thus obtained an oil which can be used without further purification for the following hydrogenation stage.

Workup

stirringAfter the suspension has been stirred for 10 hours at 20° C.
distillationthe tetrahydrofuran is distilled off in vacuo
additionWater is added to the residue, and extraction
customThere is thus obtained an oil which
customcan be used without further purification for the following hydrogenation stage

Sources & evidence

ORD record: ord-4db7c84e1eb24c088f78a0ceb966e2c1
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04725302

Linked notes

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