Bromobenzene → HCID 70552443, compound

HRID 904219Notes

Reaction equation

HRID 904219 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:20]([CH3:21])[CH2:19][CH2:18][C@@:14]4([C:15]=2[C:16]=1[OH:17])[C:9]3=[CH:10][C@@H:11]([CH3:24])[C:12]([O:22][CH3:23])=[CH:13]4.Br[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:20]([CH3:21])[CH2:19][CH2:18][C@@:14]4([C:15]=2[C:16]=1[O:17][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:9]3=[CH:10][C@@H:11]([CH3:24])[C:12]([O:22][CH3:23])=[CH:13]4

Participants

6

Reactant 3

HCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 21763808HCID 21763808, compound

Product 1

HCID 70552443HCID 70552443, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent2×

Procedure

Compound 2 (18.80 g, 42 mmol) was dried by azeotropic distillation several times with pyridine and then dissolved in pyridine (100 ml). To this solution was added bromobenzene (4.90 ml, 46 mmol), powdered potassium carbonate (6.40 g, 46 mmol) and 40μ copper powder (1.34 g, 21 mmol) and the resulting mixture refluxed under argon for 48 hours. The solution was filtered while hot, the insoluble material washed with warm pyridine and the filtrate evaporated to dryness. The residue was dissolved in benzene, treated with charcoal and evaporated to a crystalline residue. Crystallization from ethyl acetate gave 14.33 g (85%) of 3 as tan needles, mp 177°-178°. Recrystallization from ethyl acetate gave analytically pure 3, mp. 177°-178°. NMR (CDCl3): δ7.43-6.67, m(7), aromatic; 5.57, m(2), H5α and H8; 3.60, 3--OCH3 ; 3.03; 6--OCH3 ; 2.42, N--CH3 ; 1.17, d(3), 7--CH3, J=7 Hz.

Workup

  1. temperaturethe resulting mixture refluxed under argon for 48 hours
  2. filtrationThe solution was filtered while hot, the insoluble material
  3. washwashed with warm pyridine
  4. customthe filtrate evaporated to dryness
  5. dissolutionThe residue was dissolved in benzene
  6. additiontreated with charcoal
  7. customevaporated to a crystalline residue
  8. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-851366c77815403c9ca2ee2f6cfc07d4
Source dataset
uspto-grants-1980_10
Patent number
US04230712

Reaction notes

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