4-Bromopyridine → 8-Bromo-10,11-dihydro-10-(4-pyridinyl)dibenz[b,f]oxepin-10-ol
Reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C([Li])CCC.[Li]C1C=CN=CC=1.[Br:20][C:21]1[CH:22]=[CH:23][C:24]2[O:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[CH2:27][C:26](=[O:35])[C:25]=2[CH:36]=1>CCOCC.CCCCCC>[Br:20][C:21]1[CH:22]=[CH:23][C:24]2[O:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[CH2:27][C:26]([C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)([OH:35])[C:25]=2[CH:36]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Under an argon atmosphere, a solution of 4-bromopyridine (16.6 g) in anhydrous ether (90 ml) previously cooled to -40°, was transferred slowly via a cannular to a stirred solution of n-butyl lithium in hexane (1.55M; 68 ml) cooled to -78°. The mixture was stirred at -78° for 20 minutes and the resulting 4-lithiopyridine was transferred to a chilled (-78°) stirred suspension of 8-bromodibenz[b,f]oxepin-10(11H)-one (15 g) in anhydrous ether (100 ml). The reaction was stirred at -78° for 30 minutes, then the cooling bath was removed and the mixture was treated with 100 ml of water and allowed to warm to room temperature. The solids were filtered off, washed with water and dried to give 5.0 g of 8-bromo-10,11-dihydro-10-(4-pyridinyl)dibenz[b,f]oxepin-10-ol. The mother liquor was worked up and a total of 9.4 grams of the starting ketone 8-bromodibenz[b,f]oxepin-10(11H)-one were recovered.
Workup
- temperaturecooled to -78°
- temperaturea chilled (-78°)
- stirringstirred
- stirringThe reaction was stirred at -78° for 30 minutes
- customthe cooling bath was removed
- additionthe mixture was treated with 100 ml of water
- filtrationThe solids were filtered off
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-8537de479302484e9b21610f229c08e7
- Source dataset
- uspto-grants-1986_06
- Patent number
- US04595689
Reaction notes
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