Undecane → HCID 3328476, compound

HRID 2358807Notes

Reaction equation

HRID 2358807 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCCCCCCCCCC>C1(C)C=CC=CC=1>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 14257UndecaneHCID 66827Phenylboronic AcidHCID 792244-Bromo-3-nitrotoluene

Product 1

HCID 3328476HCID 3328476, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of commercially available 1-bromo-4-methyl-2-nitro-benzene (0.107 g, 0.49 mmol) in anhydrous toluene (3 mL) was added CsCO3 (0.305 g, 0.94 mmol) followed by phenylboronic acid (0.062 g, 0.49 mmol) and 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3.]undecane as a 0.1M solution in toluene (0.200 mL, 4 mole %). Nitrogen was bubbled through the resulting suspension for three minutes then palladium acetate (0.0043 g, 4 mole %) was added, the reaction vessel sealed and immersed in an 80° C. oil bath and heated for 22 hours. Subsequent filtration through celite and removal of volatiles under vacuum gave the crude product (0.105 g, 100%), which was sufficiently pure for use as isolated.

Workup

  1. customNitrogen was bubbled through the resulting suspension for three minutes
  2. additionpalladium acetate (0.0043 g, 4 mole %) was added
  3. customthe reaction vessel sealed
  4. customimmersed in an 80° C.
  5. temperatureheated for 22 hours
  6. filtrationSubsequent filtration
  7. customthrough celite and removal of volatiles under vacuum

Sources & evidence

ORD record
ord-d3d8e7db292d42ed852d80a29fd73e06
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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