Acetic Acid → 2-Methyl-5-n-propyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline

HRID 1952262Notes

Reaction equation

[CH3:1][C:2]1[CH:8]=[C:7]([C:9](F)([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[C:6]([CH2:19][CH2:20][CH3:21])=[CH:5][C:3]=1[NH2:4].[BH4-].[Na+].C(O)(=O)C>CS(C)=O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:8]=[C:7]([CH:9]([C:10]([F:11])([F:12])[F:13])[C:14]([F:16])([F:17])[F:15])[C:6]([CH2:19][CH2:20][CH3:21])=[CH:5][C:3]=1[NH2:4]

Participants

Conditions

Temperature: 60 °C

Procedure

2-Methyl-5-n-propyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline (1.6 g, 5 mmol) was dissolved in dimethyl sulfoxide (20 ml), sodium borohydride (378 mg, 10 mmol) was added by small portions, and the mixture was stirred at 60° C. for 5 hr. Ice was added to the reaction mixture by small portions, and then acetic acid was added dropwise. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed 4 times with water, dried over magnesium sulfate and concentrated under reduced pressure to give the desired compound (1.47 g).

Workup

additionIce was added to the reaction mixture by small portions
washthe organic layer was washed 4 times with water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-68fb5c4c114f485eb94e83ec689b24bb
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404861B2

Reaction notes

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