Acetonitrile → 1,2-Dibromo-3,4-dimethylbenzene

HRID 592120Notes

Reaction equation

HRID 592120 reaction equation
C(=O)(O)[O-].[NH4+].[Br:6][CH2:7][C:8]1C=[CH:12][CH:11]=[C:10](CBr)[CH:9]=1.[Br:16]CC1C=CC=CC=1CBr.BrCC1C=CC(CBr)=CC=1.BrCC1C=CC=C(CBr)N=1.BrC/C=C/CBr.[C:52](#N)[CH3:53]>O>[Br:16][C:8]1[C:7]([Br:6])=[C:52]([CH3:53])[C:11]([CH3:12])=[CH:10][CH:9]=1

Participants

9

Reactant 7

HCID 6342AcetonitrileHCID 14013Ammonium BicarbonateHCID 66665o-Bis(bromomethyl)benzeneHCID 693351,4-Bis(bromomethyl)benzeneHCID 69373Benzene, 1,3-bis(bromomethyl)-HCID 6036102,6-Bis(bromomethyl)pyridineHCID 641245trans-1,4-Dibromo-2-butene

Product 1

HCID 343431,2-Dibromo-3,4-dimethylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL flask is charged with acetonitrile (12 mL) and water (24 mL) and is degassed with argon for about 5 min. Linear peptide (0.01 mmole) and 200 mM ammonium bicarbonate (6 mL) are added followed by at least one peptide (0.012 mmole) such as, but not limited to, 1,3-bis(bromomethyl) benzene, 1,2-bis(bromomethyl)benzene, 1,4-bis(bromomethyl)benzene, 2,6-bis(bromomethyl)pyridine, (E)-1,4-dibromobut-2-ene. The reaction mixture is stirred under argon at room temperature for approximately 2 hours and monitored by LC-MS. After the reaction is complete, the reaction solution is frozen and lyophilized. HPLC purification of the crude lyophilized product followed by lyophilization of fractions containing pure peptide results in the final cyclized product as a white power.

Workup

  1. customis degassed with argon for about 5 min
  2. temperaturethe reaction solution is frozen
  3. customHPLC purification of the crude lyophilized product
  4. additioncontaining pure peptide
  5. customresults in the final cyclized product as a white power

Sources & evidence

ORD record
ord-116fd473aadb431cb20d499af6636211
Source dataset
uspto-grants-2016_01
Patent number
US09238676B2

Reaction notes

Loading…