1-Bromopentane → 4-Bromo-N,N-dipentyl-3-(trifluoromethyl)anilinato

HRID 1250005Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C)C=O>[CH2:16]([N:8]([CH2:6][CH2:5][CH2:4][CH2:10][CH3:9])[C:7]1[CH:9]=[CH:10][C:4]([Br:3])=[C:5]([C:11]([F:12])([F:13])[F:14])[CH:6]=1)[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium hydride (480 mg, 1.5 eq.) was added to a solution of 4-bromo-3-trifluoromethylaniline (1.92 g, 5 mmol) and 1-bromopentane (3 mL, 3 eq.) in dimethylformamide (10 mL) at 0° C. After 1 hour a further (320 mg, 1 eq.) of sodium hydride was added and the reaction was left overnight. The reaction was heated to 50° C. and left overnight. The reaction was quenched with methanol and partitioned between water and petroleum ether. The organic extract was concentrated under reduced pressure and the residue was purified via flash column chromatography using petroleum ether as eluent to give N,N-Dipentyl-4-bromo-3-trifluoromethylaniline (3) (2.84 g. 93%). 1H NMIR (CDCl3) 6 7.34 (d, IH, ArH); 6.80 (d, 1H, ArH); 6.52 (dd, 1H, ArH); 3.18 (t, 4H, 2×NCH2); 0.86 (t, 6H, CH˜1b). TLC (silica gel): RI˜0.55 (petroleum ether).

Workup

waitleft overnight
customThe reaction was quenched with methanol
custompartitioned between water and petroleum ether
extractionThe organic extract
concentrationwas concentrated under reduced pressure
customthe residue was purified via flash column chromatography

Sources & evidence

ORD record: ord-578b38827e764462906aabd0fc14afab
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06335446B1

Reaction notes

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