Butyl ether → HCID 87234478, compound

HRID 1513844Notes

Reaction equation

HRID 1513844 reaction equation
Br[C:2]1[S:6][C:5]2[C:7]([Br:11])=[C:8](Br)[S:9][C:4]=2[C:3]=1[Br:12].[C:13]1([Li])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O:24][CH2:25][CH2:26][CH2:27][CH3:28])CCC.[C:29](Cl)(=[O:51])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]>C1COCC1>[Br:12][C:3]1[C:4]2[S:9][C:8]([C:25](=[O:24])[CH2:26][CH2:27][CH2:28][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:13])=[C:7]([Br:11])[C:5]=2[S:6][C:2]=1[C:29](=[O:51])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]

Participants

6

Reactant 4

HCID 8909Butyl etherHCID 27625682,3,5,6-Tetrabromothieno[3,2-b]thiopheneHCID 4104741Docosanoyl chlorideHCID 178506676HCID 178506676, compound

Product 1

HCID 87234478HCID 87234478, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Di-acylation (Step A) A suspension of (2,3,5,6-tetrabromothieno[3,2,b]thiophene (20 mmol) in anhydrous THF (200 mL) is cooled to −78° C. Phenyl lithium solution in n-butyl ether (41 mmol) is added dropwise and the reaction mixture is stirred at −78° C. for 4 h. Docosanoyl chloride (41 mmol) is added to the reaction mixture via syringe while maintaining the temperature of the mixture as close to −78° C. The reaction is allowed to warm to RT over about three hours and then stirred overnight at RT. The reaction mixture is then quenched by the addition of crushed ice (200 g). The reaction mixture is stirred while the ice is allowed to melt. Most (>90%) of the THF is then removed under reduced pressure and the solid is filtered from the residual solution. The solid is suspended in water (100 mL) and stirred for 1 hr then filtered. The solid is re-suspended in methanol (100 mL), stirred for 1 hr then filtered to give the product 1-{3,6-dibromo-5-docosanoylthieno[3,2-b]thiophen-2-yl}docosan-1-one. 1H NMR (CD2Cl2) δ 0.95-1.15 (6H, m), 1.30-1.82 (76H, m) and 3.17-3.32 (4H, m).

Workup

  1. temperaturewhile maintaining the temperature of the mixture
  2. customas close to −78° C
  3. temperatureto warm to RT over about three hours
  4. stirringstirred overnight at RT
  5. customThe reaction mixture is then quenched by the addition of crushed ice (200 g)
  6. stirringThe reaction mixture is stirred while the ice
  7. customMost (>90%) of the THF is then removed under reduced pressure
  8. filtrationthe solid is filtered from the residual solution
  9. stirringstirred for 1 hr
  10. filtrationthen filtered
  11. stirringstirred for 1 hr
  12. filtrationthen filtered

Sources & evidence

ORD record
ord-9cf8397637c242c1b3d932f72b0d1a57
Source dataset
uspto-grants-2012_07
Patent number
US08217183B2

Reaction notes

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