Triethylamine → HCID 11310838, compound

HRID 1802116Notes

Reaction equation

HRID 1802116 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.CCN([CH2:16][CH3:17])CC>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2](/[CH:7]=[CH:2]/[CH2:3][CH2:4][CH2:5][CH2:6][CH2:16][CH3:17])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 114661-Bromo-4-nitrobenzene

Product 1

HCID 11310838HCID 11310838, compoundYield 181.8%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

1-bromo-4-nitrobenzene (2.01 g, 10 mmol), 1-ocetene (7.8 mL, 50 mmol), and Pd(OAc)2 (50 mg, 0.2 mmol) were stirred for 10 min under nitrogen atmosphere. Then tri-o-tolylphosphine (24 mg, 0.8 mmol) was added to the mixture and stirred for 10 min. Et3N (5.5 mL, 40 mmol) was then added to the mixture. The mixture was heated to 110° C. for 18 h. Water was added to the mixture and extracted with EtOAc. The organic layer was concentrated and purified by silica gel chromatography using PE as eluent to give compound the title compound (2.121 g, 90%). 1H NMR (300 MHz, CDCl3) δ 8.097 (d, 2H), 7.235 (d, 2H), 6.442 (s, 1H), 5.976-5.377 (m, 1H), 2.231-2.052 (m, 2H), 1.710-1.246(m, 8H), 0.850 (t, 3H).

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe organic layer was concentrated
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-62b397bfc18c4a6699da0b423aeb1b60
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

Loading…