Stannous Chloride → HCID 57995463, compound

HRID 423441Notes

Reaction equation

HRID 423441 reaction equation
[Sn](Cl)Cl.[CH:4]([Si:7]([C:14]#[C:15][C:16]1(O)[C:27]2[C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[S:24][C:23]=2[C:22]([C:33]#[C:34][Si:35]([CH:42]([CH3:44])[CH3:43])([CH:39]([CH3:41])[CH3:40])[CH:36]([CH3:38])[CH3:37])(O)[C:21]2[C:20]3[CH:45]=[CH:46][CH:47]=[CH:48][C:19]=3[S:18][C:17]1=2)([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])([CH3:6])[CH3:5]>C(O)(=O)C.CC(C)=O>[CH:36]([Si:35]([C:34]#[C:33][C:22]1[C:21]2[C:20]3[CH:45]=[CH:46][CH:47]=[CH:48][C:19]=3[S:18][C:17]=2[C:16]([C:15]#[C:14][Si:7]([CH:4]([CH3:6])[CH3:5])([CH:8]([CH3:10])[CH3:9])[CH:11]([CH3:13])[CH3:12])=[C:27]2[C:23]=1[S:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=12)([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:40])[CH3:41])([CH3:37])[CH3:38]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 57995447HCID 57995447, compound

Product 1

HCID 57995463HCID 57995463, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of tin(II)chloride dehydrate (2.59 g, 11.5 mmol) in 50% acetic acid (40 ml) is added within ten minutes to a solution of 6,12-bis-[(triisopropylsilanyl)-ethynyl]-6,12-dihydro-dibenzo[d,d′]benzo[1,2-b;4,5-b′]dithiophene-6,12-diol (educt 3) in acetone (35 ml). There is a slight temperature increase (2-3° C.), and formation of a yellow suspension takes place. This suspension is stirred over night at ambient temperature, and then the solid is filtered off. The solid is then washed with 50% acetic acid (30 ml), water (twice with 40 ml), and acetone (2*40 ml). The residue is then dried to give crude product which is recrystallised from toluene (15 ml). The product is filtered off, washed with toluene (10 ml), and hexane (10 ml). After drying, the title product is obtained as pale yellow crystals. Mp. (DSC) 155° C. (broad probably phase transition), 208° C. (sharp, probably melting point). 1H-NMR (CDCl3, 300 MHz) δ 1.31-1.336 (m (higher order), 21H, CH(CH3)2); 7.48 (m, 1H, H-2), 7.53 (m, 1H, H-3), 7.92 (d, 1H, H-4); 9.37 (d, 1H, H-1). 13C-NMR (CDCl3, 75 MHz) δ 11.92 (CH); 19.22 (CH3); 103.42, 106.36 (C≡C); 112.56 (C-6); 122.78 (C-4); 124.33 (C-2); 125.16 (C-1); 127.46 (C-3); 132.78 (C-6a); 135.49 (C-6b); 140.47 (C-4-a); 143.30 (C-5a).

Workup

  1. filtrationthe solid is filtered off
  2. washThe solid is then washed with 50% acetic acid (30 ml), water (twice with 40 ml), and acetone (2*40 ml)
  3. customThe residue is then dried
  4. customto give crude product which
  5. customis recrystallised from toluene (15 ml)
  6. filtrationThe product is filtered off
  7. washwashed with toluene (10 ml), and hexane (10 ml)
  8. customAfter drying

Sources & evidence

ORD record
ord-c6ec562a419743fca54d779984d60fd8
Source dataset
uspto-grants-2012_01
Patent number
US08101776B2

Reaction notes

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