Iodine → HCID 22743689, compound

HRID 1646690Notes

Reaction equation

HRID 1646690 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[Mg].II.Br[C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=1>C(OCC)C>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 807IodineHCID 79271,3-DibromobenzeneHCID 138512-BromothiopheneHCID 5462224Magnesium

Product 1

HCID 22743689HCID 22743689, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

The Grignard was prepared by adding 2-bromothiophene (8.15 g, 0.05 m) in diethyl ether (10 ml) to magnesium turnings (1.22 g, 0.05 m) and iodine (trace) in diethyl ether (15 ml). After 1 h, the Grignard was slowly added to 1,3-dibromobenzene (5.0 g, 0.021 m) and catalyst in diethyl ether (20 ml). Workup after 24 h afforded a residue which crystallized from hot hexanes yielding a green solid (540 mg, 10% crude yield). The green solid (190 mg) was purified by column chromatography using petroleum ether as the eluant. A light green crystalline solid (136 mg, 7.6% yield) was separated; m.p. 83°-84° C., m/z 242 (M+); Found: C, 69.22; H, 4.04; S, 26.09; C14H10S2 requires: C,69.4; H, 4,1; S, 26.4H NMR(CDCl3) δ7.35 (dd, J=<1, 3 Hz, 2 H), δ7.085 (dd, J=5,3 Hz, 2H), δ7.29 (dd, J=<1, 5 Hz, 2H), δ7.81 (t, J=<1 Hz, 1H), δ7.38 (dd, J=8 Hz, 1H), δ7.51 (ddd, J=<1,2, 8 Hz, 2H).

Workup

  1. customThe Grignard was prepared
  2. customWorkup after 24 h afforded a residue which
  3. customcrystallized from hot hexanes yielding a green solid (540 mg, 10% crude yield)
  4. customThe green solid (190 mg) was purified by column chromatography

Sources & evidence

ORD record
ord-790265aa179d4f1c93887227309375ba
Source dataset
uspto-grants-1993_01
Patent number
US05180838

Reaction notes

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