Bromine → 9-Bromomethyl-6,11-dihydro-11-oxodibenz[b,e]oxepin

HRID 894190Notes

Reaction equation

HRID 894190 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][O:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[O:16])[C:6]=2[CH:17]=1.[Br:18]Br>BrCCBr.[W]>[Br:18][CH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][O:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[O:16])[C:6]=2[CH:17]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 211627129-Methyl-6,11-dihydro-11-oxodibenz[b,e]oxepin

Product 1

HCID 211627239-Bromomethyl-6,11-dihydro-11-oxodibenz[b,e]oxepin

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 78391,2-DibromoethaneSolvent2×

Procedure

To a stirred and irradiated (Tungsten lamp) solution of 2.0 gm of the 9-methyl compound of Step B in 5 ml of 1,2-dibromoethane, add a solution of 1.7 gm of bromine in 5 ml of 1,2-dibromoethane dropwise over a period of 1 hour at 150° C. Cool the reaction mixture, pour into ice water and extract with water and dry over sodium sulfate. Concentrate to dryness and crystallize the residue from isopropyl ether to obtain the title product.

Workup

  1. temperatureCool the reaction mixture
  2. extractionextract with water
  3. dry with materialdry over sodium sulfate
  4. concentrationConcentrate to dryness
  5. customcrystallize the residue from isopropyl ether

Sources & evidence

ORD record
ord-e89b81fa23844afb95cbe6a582941ca0
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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