Stannous chloride dihydrate → HCID 57995441, compound

HRID 423444Notes

Reaction equation

HRID 423444 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2(O)[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:17]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][CH:28]=3)(O)[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>CC(C)=O.O.C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C:10]2[C:23]3[C:18]([C:17]([C:25]#[C:26][C:27]4[CH:28]=[CH:29][C:30]([Br:33])=[CH:31][CH:32]=4)=[C:16]4[C:11]=2[CH:12]=[CH:13][CH:14]=[CH:15]4)=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 66673796HCID 66673796, compound

Product 1

HCID 57995441HCID 57995441, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a suspension of 9,10-bis-(4-bromo-phenylethynyl)-9,10-dihydro-anthracene-9,10-diol (2.0 g, 3.5 mmol) in aceton (25 ml), a solution of tin(II)chloride dihydrate (1.82 g, 8.05 mmol) in a mixture of water (15 ml) and acetic acid (15 ml) is added within 15 minutes. The obtained suspension is stirred for another 2.5 hours at ambient temperature, and then the solid is filtered off to give a first crop the title compound. Over night another crop of product crystallizes from the mother liquors, and the combined crops are recrystallized from anisol (30 ml) to give the title compound as orange needles. DSC: mp=305° C. MS: 534 (correct isotope pattern). Elementary analysis: C, 67.45; (calcd. 67.19); H, 3.23; (calcd. 3.01).

Workup

  1. additionis added within 15 minutes
  2. filtrationthe solid is filtered off

Sources & evidence

ORD record
ord-9aab251f323542478782cd991618e9bc
Source dataset
uspto-grants-2012_01
Patent number
US08101776B2

Reaction notes

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