Diethyl Ether → HCID 68618174, compound

HRID 2201339Notes

Reaction equation

HRID 2201339 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-50a550c4ffc6410a80b8754df65cad27
Source dataset
uspto-grants-2016_06
Patent number
US09362505B2

Reaction notes

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