4,4'-Dibromobiphenyl → HCID 68193299, compound

HRID 1626828Notes

Reaction equation

HRID 1626828 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:15][C@H:16]1[CH2:18][O:17]1.[Cl-].[NH4+]>O1CCCC1>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH2:15][C@@H:16]([OH:17])[CH3:18])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 71104,4'-DibromobiphenylHCID 25517Ammonium ChlorideHCID 146262(2S)-2-Methyloxirane

Product 1

HCID 68193299HCID 68193299, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4,4′-Dibromobiphenyl (0.62 g, 2.0 mmol) was dissolved in tetrahydrofuran (5 mL), and a solution of tri-n-butylmagnesium lithium in tetrahydrofuran was added under a nitrogen atmosphere at 0° C., which was stirred at the same temperature for 1 hour, followed by addition of (2S)-2-methyloxirane (0.15 mL, 2.2 mmol). The temperature of the reaction solution was raised to room temperature, followed by stirring for 30 minutes, and subsequently a saturated aqueous ammonium chloride solution was added, followed by extraction with ethyl acetate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.40 (hexane/ethyl acetate=2/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.23 g, 0.79 mmol) as a white solid (yield 39%).

Workup

  1. stirringby stirring for 30 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. distillationAfter the solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  5. concentrationa fraction corresponding to the Rf value=0.40 (hexane/ethyl acetate=2/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8288bffcb32144cabb16481a608184e3
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

Loading…