2-Chloroaniline → 1,4-Dimethoxy-9H-carbazole

HRID 1752217

Reaction equation

HRID 1752217 reaction equation
CC([O-])(C)C.[Na+].Cl[C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10].Br[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[O:24][CH3:25]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:25][O:24][C:17]1[C:16]2[NH:10][C:9]3[C:8](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:21]=2[C:20]([O:22][CH3:23])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 72402-ChloroanilineHCID 91353Benzene, 2-bromo-1,4-dimethoxy-HCID 23676156Sodium t-butoxide

Product 1

HCID 145293041,4-Dimethoxy-9H-carbazoleYield 55%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
170 °C

Procedure

Following a published procedure (Bedford, R. B.; Betham, M. J. Org. Chem. 2006, 71, 9403-9410), NaOtBu (0.754 g, 7.84 mmol), Pd(OAc)2 (0.014 g, 0.06 mmol), and [HPtBu3][BF4] (0.023 g, 0.078 mmol) were suspended in dry toluene (5 mL) in a microwave vial. 2-Chloroaniline (0.165 mL, 1.567 mmol) and 2-bromo-1,4-dimethoxybenzene (0.240 mL, 1.598 mmol) were then added, and the vial was sealed. The reaction was then heated in the microwave reactor at 170° C. for 4 h, allowed to cool, and then quenched by addition of 1M HCl. The aqueous phase was extracted with CH2Cl2, the organic layer was dried over Na2SO4, filtered and condensed. The crude mixture was purified by chromatography (SiO2, 0-10% EtOAc/Hexane) to afford the title product (0.193 g, 55%).

Workup

  1. customthe vial was sealed
  2. temperatureto cool
  3. customquenched by addition of 1M HCl
  4. extractionThe aqueous phase was extracted with CH2Cl2
  5. dry with materialthe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customcondensed
  8. customThe crude mixture was purified by chromatography (SiO2, 0-10% EtOAc/Hexane)

Sources & evidence

ORD record
ord-ac1c7dee59534fefb9bcc2c5e62e4deb
Source dataset
uspto-grants-2015_10
Patent number
US09162980B2

Linked notes

Loading…