Bromine → HCID 20375728, compound

HRID 1448815Notes

Reaction equation

HRID 1448815 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH:13]=[CH:12][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:19]Br.N1(C2CCCCCCC2)CCCCCCN1>C(Cl)(Cl)(Cl)Cl.CC(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH:13]=[C:12]([Br:19])[C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 24408BromineHCID 20375726HCID 20375726, compoundHCID 66583054Diazabicyclooctane

Product 1

HCID 20375728HCID 20375728, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2.53 g (10 m mole) of methyl 3-(tert-butoxycarbonylamino)-1,5-cyclohexadienecarboxylate in 40 ml of carbontetrachloride at 0° C. is treated dropwise with 1.60 g (10 m mole) of bromine. The solution is stirred at 25° C. for 12 hours, then evaporated under reduced pressure to afford the crude dibromide which is dissolved in 40 ml of acetone and treated with 1.2 g (10 m mole) of diazabicyclooctane for 12 hours at 25° C. The solvent is evaporated under reduced pressure, and the residue is treated with ether and water. The organic phase is dried and evaporated to afford methyl 3-tert-butoxycarbonylamino-6-bromo-1,5-cyclohexadienecarboxylate.

Workup

  1. customevaporated under reduced pressure
  2. customto afford the crude dibromide which
  3. customThe solvent is evaporated under reduced pressure
  4. additionthe residue is treated with ether and water
  5. customThe organic phase is dried
  6. customevaporated

Sources & evidence

ORD record
ord-a7aba82a2d1e4e40ab4d01e1fb80513e
Source dataset
uspto-grants-1980_02
Patent number
US04187316

Reaction notes

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