Diethyl Ether → HCID 68618174, compound

HRID 340857Notes

Reaction equation

HRID 340857 reaction equation
Br[C:2]1[S:6][C:5]2[C:7]3[S:8][C:9](Br)=[CH:10][C:11]=3[C:12]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:4]=2[CH:3]=1.C(O[CH2:28][CH3:29])C>>[C:4]1([C:2]2[S:6][C:5]3[C:7]4[S:8][C:9]([C:29]5[CH:28]=[CH:17][CH:16]=[CH:15][CH:14]=5)=[CH:10][C:11]=4[C:12]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:4]=3[CH:3]=2)[CH:13]=[CH:12][CH:11]=[CH:7][CH:5]=1

Participants

3

Reactant 2

HCID 3283Diethyl EtherHCID 68616863HCID 68616863, compound

Product 1

HCID 68618174HCID 68618174, compoundYield 67%

Procedure

A reaction was carried out in the same manner as in Example 11, except that 2,7-dibromo-4,5-di(n-pentyl)benzo[2,1-b:3,4-b′]dithiophene (124.9 mg (0.26 mmol)) was used instead of 2,7-dibromo-4,5-di(n-propyl)benzo[2,1-b:3,4-b′]dithiophene. The post-reaction solution was charged with diethyl ether (about 20 mL), and the resultant solution was then washed with water. Subsequently, the organic layer was dried over sodium sulfate, and then filtered. The solvent was removed from the filtrate by distillation, and then the remaining solid was purified by thin-layer column chromatography using hexane as a developing solvent to obtain the target product 2,7-diphenyl-4,5-di(n-pentyl)benzo[2,1-b:3,4-b′]dithiophene as a yellow solid (83.8 mg, 67% yield). The obtained target product 1H-NMR and HRMS measurement results were as follows.

Workup

  1. washthe resultant solution was then washed with water
  2. dry with materialSubsequently, the organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed from the filtrate by distillation
  5. customthe remaining solid was purified by thin-layer column chromatography

Sources & evidence

ORD record
ord-1ee6032f01e146e18cd461209a790bf9
Source dataset
uspto-grants-2014_11
Patent number
US08895692B2

Reaction notes

Loading…