Bromobenzene → HCID 69639913, compound

HRID 2188229Notes

Reaction equation

HRID 2188229 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:12][C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:4].Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[CH3:1][O:2][C:3]([CH:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[N:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:13]2[C:18]1=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:4]

Participants

8

Reactant 3

HCID 7961BromobenzeneHCID 22084703HCID 22084703, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 69639913HCID 69639913, compoundYield 72.8%

Reagents, catalysts & solvents 4

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.00 g of acridan-9-carboxylic acid methyl ester (4.18 mmol), 0.44 mL of bromobenzene (4.18 mmol), 0.60 g of sodium t-butoxide (6.27 mmol), 23 mg of Pd(OAc)2 (0.105 mmol), and 17 mg of tri-t-butylphosphine (0.084 mmol) in 15 mL of toluene was stirred under inert atmosphere at room temperature. After 2.5 h, 5 g of silica gel in 15 mL of CH2Cl2 was added to the reaction mixture. The slurry was filtered, washed with excess CH2Cl2 and the filtrate was concentrated to a thick solution. 20 mL of hexanes was added to this solution, causing a white precipitate to form. The precipitate was filtered, washed with hexanes, and dried to afford 0.96 g of N-phenylacridan-9-carboxylic acid methyl ester (72%).

Workup

  1. filtrationThe slurry was filtered
  2. washwashed with excess CH2Cl2
  3. concentrationthe filtrate was concentrated to a thick solution
  4. addition20 mL of hexanes was added to this solution
  5. customto form
  6. filtrationThe precipitate was filtered
  7. washwashed with hexanes
  8. customdried

Sources & evidence

ORD record
ord-9a41e5821ed64899b3b11d3bc842e79b
Source dataset
uspto-grants-2002_06
Patent number
US06410732B2

Reaction notes

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