Bromine → HCID 19760189, compound

HRID 1586911Notes

Reaction equation

HRID 1586911 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][C:4]([CH3:14])([CH3:13])[C:3]1=[O:15].[Br:16]Br>C(Cl)Cl.[Fe]>[Br:16][C:11]1[CH:10]=[CH:9][C:8]2[N:2]([CH3:1])[C:3](=[O:15])[C:4]([CH3:13])([CH3:14])[CH2:5][CH2:6][C:7]=2[CH:12]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 19760206HCID 19760206, compound

Product 1

HCID 19760189HCID 19760189, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 18.0 g of 2,3,4,5-tetrahydro-1,3,3-trimethyl-2-oxo-1H-1-benzazepine in 250 ml of methylene chloride was treated with 2.0 g of iron powder and thereafter dropwise with 5.83 ml of bromine in 30 ml of methylene chloride. The reaction mixture was heated to reflux overnight, thereafter poured on to ice, extracted with diethyl ether, washed with sodium pyro- sulphite solution, water and saturated sodium chloride solution, dried and evaporated. Crystallization from ethyl acetate/n-hexane yielded 21.4 g of pure 7-bromo-2,3,4,5-tetrahydro-1,3,3-trimethyl-2-oxo-1H-1-benzazepine.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. additionpoured on to ice
  4. extractionextracted with diethyl ether
  5. washwashed with sodium pyro- sulphite solution, water and saturated sodium chloride solution
  6. customdried
  7. customevaporated
  8. customCrystallization from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-230472a7b43c499d853f061539caab04
Source dataset
uspto-grants-1993_06
Patent number
US05216148

Reaction notes

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