1-(Bromomethyl)-3-(trifluoromethyl)benzene → HCID 19955619, compound

HRID 1109083Notes

Reaction equation

HRID 1109083 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br.[C:13]1([CH3:22])[CH:18]=[CH:17][C:16]([S:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.[Na+]>CN(C=O)C.O>[CH3:22][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:12])([F:11])[F:1])[CH:4]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 19955619HCID 19955619, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Trifluoromethylbenzyl bromide (50 mmole) and sodium p-toluenesulfinate (65 mmole) were dissolved in 100 mL of dry DMF. The mixture was stirred at about 23° for about 18 hours then diluted with water. The sulfone crystallized from the aqueous mixture and was filtered. The compound was purified by recrystallization (EtOH). Colorless plates, mp 139°-140°: IR (KBr) 2954, 1614, 1598, 1450, 1332, 1312, 1288, 1164, 1142, 1116, 1074 cm-1 ; 1H NMR (CDCl3) δ 2.44 (s, 3H), 4.34 (s, 2H), 7.16 (s, 1H), 7.26 (d, J=8.1 Hz, 2H), 7.42 (m, 1H), 7.50 (d, J=8.1 Hz, 2H), 7.58 (d, J=7.5 Hz, 1H); MS m/e 315 (MH+).

Workup

  1. customThe sulfone crystallized from the aqueous mixture
  2. filtrationwas filtered
  3. customThe compound was purified by recrystallization (EtOH)

Sources & evidence

ORD record
ord-4b28963ee8424cb0bddaa59db0b07419
Source dataset
uspto-grants-1994_06
Patent number
US05318993

Reaction notes

Loading…