O-Toluidine → 4-[1-(Bromo-difluoro-methyl)-1,2,2,2-tetrafluoro-ethyl]-2-methyl-phenylamine

HRID 1824581

Reaction equation

S(S([O-])=O)([O-])=O.[Na+].[Na+].[NH2:9][C:10]1[C:11]([CH3:16])=[CH:12][CH:13]=[CH:14][CH:15]=1.C(=O)([O-])O.[Na+].[Br:22][C:23]([F:32])([F:31])[C:24](Br)([F:29])[C:25]([F:28])([F:27])[F:26].C(=O)([O-])[O-].[Na+].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.COC(C)(C)C.O>[CH3:16][C:11]1[CH:12]=[C:13]([C:24]([F:29])([C:25]([F:28])([F:27])[F:26])[C:23]([Br:22])([F:32])[F:31])[CH:14]=[CH:15][C:10]=1[NH2:9]

Participants

Conditions

Temperature: 40 °C

Procedure

First 154.36 g (0.887 mol) of sodium dithionite and then 50 g (0.467 mol) of o-toluidine (2-methylaniline) were added at room temperature to a mixture of 900 ml of water, 350 ml of tert-butyl methyl ether, 74.48 g (0.887 mol) of sodium hydrogencarbonate and 12.68 g of tetra-n-butylammonium hydrogensulphate. Subsequently, a solution of 274.684 g of 1,2-dibromo-1,1,2,3,3,3-hexafluoropropane in 100 ml of tert-butyl methyl ether was added dropwise at 35–40° C. and, on completion of addition, the mixture was stirred at 40° C. for a further 18 h. If necessary, sodium carbonate was used to adjust to a pH of 5 and the organic phase was removed, dried and concentrated. The remaining residue is incipiently distilled under reduced pressure at 0.3 mbar up to an internal temperature of 100° C.

Workup

customthe organic phase was removed
customdried
concentrationconcentrated
distillationThe remaining residue is incipiently distilled under reduced pressure at 0.3 mbar up to an internal temperature of 100° C.

Sources & evidence

ORD record: ord-d062f89ffb4a489990a2eedd0881b43c
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07041852B2

Linked notes

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