Water → 3,3'-[2-(2-Bromophenyl)ethane-1,1-diyl]dipyridine

HRID 1686083Notes

Reaction equation

HRID 1686083 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([N-]C(C)C)(C)C.[Li+].[Br:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Br.O>C1COCC1.C1CCCCC1>[Br:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25][CH:1]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 769652-Bromobenzyl bromideHCID 2724682Lithium diisopropylamideHCID 147626403,3'-Methylenedipyridine

Product 1

HCID 672646383,3'-[2-(2-Bromophenyl)ethane-1,1-diyl]dipyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3,3′-methylenedipyridine (5.0 g, 29.4 mmol) in THF (300 mL) at 0° C. was treated with lithium diisopropylamide (39 mL of a 1.5 M solution of the mono-THF complex in cyclohexane, 58.7 mmol) dropwise over 10 min. After stirring at 0° C. for 30 min, 2-bromobenzylbromide (7.3 g as a solution in 100 mL THF, 29.4 mmol) was added dropwise via cannula. The reaction mixture was stirred for 1 h at 0° C. before being poured into H2O (300 mL) and extracted with CH2Cl2 (3×300 mL). The organic extracts were pooled, washed with saturated aqueous NaCl (2×200 mL), dried (Na2SO4), and concentrated under reduced pressure to provide 3,3′-[2-(2-bromophenyl)ethane-1,1-diyl]dipyridine. ESI+MS: 339.0 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred for 1 h at 0° C.
  2. extractionextracted with CH2Cl2 (3×300 mL)
  3. washwashed with saturated aqueous NaCl (2×200 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ee00eb1d2c84c76977c7496262fe530
Source dataset
uspto-grants-2012_04
Patent number
US08148535B2

Reaction notes

Loading…