Toluene → HCID 18185235, compound

HRID 1358544Notes

Reaction equation

HRID 1358544 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][C:9]([CH3:13])([CH3:12])[CH2:8][C:7](=[O:14])[C:6]=2[CH:15]=1.[C:16]1(C)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[NH4+]>O.C(O)C>[CH3:12][C:9]1([CH3:13])[CH2:8][C:7](=[O:14])[C:6]2[CH:15]=[C:2]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:3]=[CH:4][C:5]=2[O:11][CH2:10]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium Carbonate2×HCID 14923Ammonium HydroxideHCID 18185243HCID 18185243, compound

Product 1

HCID 18185235HCID 18185235, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

8.5 g of 7-bromo-3,3-dimethyl-3,4-dihydro-2H-benzoxepin-5-one (0.0316 mol), 95 ml of toluene, 34.7 ml of a 2M sodium carbonate solution, 46 ml of ethanol, 4.19 g of phenyboric [sic] acid (0.0344 mol, 1.09 equivalents) and 0.677 g of tetrakis(triphenyl-phosphine)palladium are changed to a 250 ml reactor. The reaction mixture is brought to reflux for 8 h and is then allowed to return to room temperature. The reaction mass is poured into a mixture of 70 ml of water, 56.8 ml of a 30% aqueous ammonium hydroxide solution and 78 ml of a 2M aqueous sodium carbonate solution. The catalyst is filtered off through silica. Extraction is then carried out 3 times with 100 ml of ethyl acetate and the organic phases are washed with 3 times 100 ml of water and dried over anhydrous sodium sulphate before being concentrated under reduced pressure. 14 g of an oil are isolated, which oil is purified by column chromatography using a 4/1 hexane/ethyl acetate mixture. 8.5 g of the title compound are thus obtained in the form of a liquid.

Workup

  1. temperatureto reflux for 8 h
  2. customto return to room temperature
  3. filtrationThe catalyst is filtered off through silica
  4. extractionExtraction
  5. washthe organic phases are washed with 3 times 100 ml of water
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationbefore being concentrated under reduced pressure

Sources & evidence

ORD record
ord-0df5da106265403db24af4079501f492
Source dataset
uspto-grants-2003_07
Patent number
US06596758B1

Reaction notes

Loading…