1,6-Dibromohexane → 4'-(7-Bromoheptyl)-2,2';6',2''-terpyridine

HRID 29031Notes

Reaction equation

HRID 29031 reaction equation
C[CH:2]1[CH2:7][CH2:6][CH2:5][N:4](C)[C:3]1([CH3:10])C.C([Li])CCC.[CH3:16][C:17]1[CH:22]=C[N:20]=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25](C3C=CC=CN=3)[N:24]=2)[CH:18]=1.Br[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][Br:42]>C1COCC1.C(OC(=O)C)C>[Br:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:22][C:17]1[CH:18]=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[N:20]=[C:10]([C:3]2[CH:2]=[CH:7][CH:6]=[CH:5][N:4]=2)[CH:16]=1

Participants

7

Reactant 4

HCID 123681,6-DibromohexaneHCID 187617721,2,2,3-TetramethylpiperidineHCID 668218454'-Methyl-2,2';6,2''-terpyridine2×HCID 178418339Butyllithium

Product 1

HCID 692166004'-(7-Bromoheptyl)-2,2';6',2''-terpyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

0.5 ml of tetramethylpiperidine (3 mmol) and 20 ml of anhydrous THF were put into a 100 ml Schlenk flask and stirred well. After the resultant material was cooled using liquid nitrogen and ethylacetate to −78□, 1.88 mL of normal butyllithium (3 mmol, 1.6 M hexane solution) was added dropwise slowly using an injector. 15 ml of THF, in which 0.5 g of the compound synthesized in Example 2 (compound 221 in FIG. 2, 2 mmol) was dissolved, was put into the flask using an injector at −78□. After being stirred at −78□ for 30 minutes, the resultant material was added dropwise slowly into 1 ml of a 1,6-dibromohexane solution (4 mmol), in which 50 ml of THF was diluted, using a cannula at −78□. After being stirred at −78□ for 12 hours, the resultant material was distilled under reduced pressure to be a saturation solution. Next, the resultant material was refined using column chromatography (developer: THF/normal hexane=⅓) to obtain a compound 4′-(7-bromoheptyl)-2,2′;6′,2″-terpyridine (intermediate compound 231 in FIG. 2) with a yield of 76%.

Workup

  1. additionwas added dropwise slowly
  2. stirringAfter being stirred at −78□ for 30 minutes
  3. additionwas diluted
  4. stirringAfter being stirred at −78□ for 12 hours
  5. distillationthe resultant material was distilled under reduced pressure

Sources & evidence

ORD record
ord-0afcf9de02ff4e97809a7ddb9d47151a
Source dataset
uspto-grants-2008_09
Patent number
US07420058B2

Reaction notes

Loading…