Bromobenzene → HCID 10266074, compound

HRID 2188232Notes

Reaction equation

HRID 2188232 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C:8]3[C:13]([NH:14][C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CC(C)([O-])C.[Na+].Br[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C(Cl)Cl>[C:37]1([N:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][C:15]2=3)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

8

Reactant 4

HCID 7961BromobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 69640155HCID 69640155, compound

Product 1

HCID 10266074HCID 10266074, compoundYield 83.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 13.0 g of 3-methoxyacridan (57.7 mmol), 259 mg of Pd(OAc)2 (1.15 mmol), 187 g of tri-t-butylphosphine (0.92 mmol), 8.32 g of sodium t-butoxide (86.6 mmol), and 10.9 g of bromobenzene (69.2 mmol) in 100 mL of dry toluene was stirred under inert atmosphere at room temperature for 18 h. The reaction mixture was poured into a mixture of 300 mL of CH2Cl2 and 100 g of silica gel. The mixture was filtered, washed with an additional 500 mL of CH2Cl2, and the solids were discarded. The filtrate was concentrated in vacuo to afford a yellow solid. The solid was triturated in 100 mL of hexanes, filtered, washed with an additional 100 mL of hexanes, and dried to afford 13.8 g of N-phenyl-3-methoxyacridan, by NMR analysis (83%).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with an additional 500 mL of CH2Cl2
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford a yellow solid
  5. customThe solid was triturated in 100 mL of hexanes
  6. filtrationfiltered
  7. washwashed with an additional 100 mL of hexanes
  8. customdried

Sources & evidence

ORD record
ord-066ae5e7420a4870ada6aca05fecfb4f
Source dataset
uspto-grants-2002_06
Patent number
US06410732B2

Reaction notes

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