Triethylamine → HCID 11310838, compound

HRID 709900Notes

Reaction equation

HRID 709900 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-7ce7094e2c304f22b222e239bc384c8e
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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