Trimethyltin chloride → HCID 86688834, compound

HRID 870113Notes

Reaction equation

HRID 870113 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[S:8][C:9]3[N:10]=[C:11]([C:15]4[S:16][C:17](Br)=[CH:18][C:19]=4[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[S:12][C:13]=3[N:14]=2)=[C:4]([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][CH3:48])[CH:3]=1.C([Li])CCC.[CH3:54][Sn:55](Cl)([CH3:57])[CH3:56]>C(OCC)C>[CH3:54][Sn:55]([CH3:57])([CH3:56])[C:2]1[S:6][C:5]([C:7]2[S:8][C:9]3[N:10]=[C:11]([C:15]4[S:16][C:17]([Sn:55]([CH3:57])([CH3:56])[CH3:54])=[CH:18][C:19]=4[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[S:12][C:13]=3[N:14]=2)=[C:4]([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][CH3:48])[CH:3]=1

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 66610519HCID 66610519, compoundHCID 178418339Butyllithium

Product 1

HCID 86688834HCID 86688834, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a 100 mL Schlenk flask was placed 250 mg (0.29 mmol) of 2,5-bis(5-bromo-3-tetradecyl-2-thienyl)-thiazolo[5,4-d]thiazole. The flask was evacuated and refilled with Ar three times. 35 mL of dry THF was added to the flask. The flask was subsequently cooled to −78° C. n-Butyl lithium (0.64 mmol) was then added dropwise to the above solution. After the solution was stirred at −78° C. for 1 hour, 0.7 mL of 1.0 M solution of trimethyl tin chloride was syringed into the reaction mixture. After the solution was allowed to warm up to room temperature, 100 mL of diethyl ether was added to the solution. The solution was washed three times with 100 mL of water and then the organic layer was dried over anhydrous MgSO4. After the solvent was removed in vacuum, 2,5-bis(5-trimethylstannyl-3-tetradecyl-2-thienyl)-thiazolo[5,4-d]thiazole was isolated in quantitative yield.

Workup

  1. customTo a 100 mL Schlenk flask was placed
  2. customThe flask was evacuated
  3. additionrefilled with Ar three times
  4. addition35 mL of dry THF was added to the flask
  5. additionwas then added dropwise to the above solution
  6. temperatureto warm up to room temperature
  7. washThe solution was washed three times with 100 mL of water
  8. dry with materialthe organic layer was dried over anhydrous MgSO4
  9. customAfter the solvent was removed in vacuum

Sources & evidence

ORD record
ord-731f3591ccbc441fbb6dd50048a314b4
Source dataset
uspto-grants-2015_03
Patent number
US08969508B2

Reaction notes

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