1,2-Dibromoethane → HCID 23135783, compound

HRID 2117817Notes

Reaction equation

HRID 2117817 reaction equation
Br[CH2:2][CH2:3]Br.[Cl-].[NH4+:6].O1[CH2:11][CH2:10][CH2:9][CH2:8]1>>[C:8]1([C:8]2[N:6]=[C:8]([CH2:9][CH2:10][C:11]3[CH:11]=[CH:10][CH:9]=[C:8]([C:3]4[CH:2]=[CH:11][CH:10]=[CH:9][CH:8]=4)[N:6]=3)[CH:11]=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 78391,2-DibromoethaneHCID 8028TetrahydrofuranHCID 25517Ammonium Chloride

Product 1

HCID 23135783HCID 23135783, compoundYield 65.1%

Conditions

Temperature
-78 °C

Procedure

The tetrahydrofuran (12 ml) solution of 2-methyl-6-phenylpyridine (1.0 g, 5.9 mmol) obtained by Reference Example 10 was cooled to −78° C., then lithium diisopropylamide tetrahydrofuran solution obtained as above was dropwise added thereto while 15 minutes. The reaction mixture was additionally stirred at −78° C. for 1 hour, then a tetrahydrofuran (10 ml) solution of 1,2-dibromoethane (510 μL, 5.9 mmol, 1 equivalent) was dropwise added thereto, the reaction temperature was allowed to warm to 0° C. while 40 minutes. Then the reaction mixture was poured into an aqueous saturated ammonium chloride solution, an organic layer was separated, furthermore an aqueous layer was extracted with toluene. The organic layer was combined, and the solvent was distilled off, and the residue was purified by silica gel column chromatography and recrystallization, thereby obtaining 646 mg of 1,2-bis(6-phenylpyridine-2-yl)ethane as white powder. Yield: 65.1%.

Workup

  1. additionabove was dropwise added
  2. temperatureto warm to 0° C. while 40 minutes
  3. customan organic layer was separated
  4. extractionfurthermore an aqueous layer was extracted with toluene
  5. distillationthe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography and recrystallization

Sources & evidence

ORD record
ord-5dee9769198c40cba77686190516ceac
Source dataset
uspto-grants-2008_10
Patent number
US07442797B2

Reaction notes

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