Iodine → Thiophene, 2-(1-naphthalenyl)-

HRID 1646691Notes

Reaction equation

HRID 1646691 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[Mg].II.Br[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1>C(OCC)C>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:19]1[C:20]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 807IodineHCID 70011-BromonaphthaleneHCID 138512-BromothiopheneHCID 5462224Magnesium

Product 1

HCID 3014303Thiophene, 2-(1-naphthalenyl)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

2-Bromothiophene (1.45 ml, 0.015 m) in diethyl ether (20 ml) was added slowly to magnesium turnings (0.48 g, 0.02 m) and iodine (trace) in diethyl ether (10 ml). It was stirred for 30 min before being added to 1-bromonaphthalene (2.07 g, 0.01 m) and catalyst in diethyl ether (25 ml). The reaction was worked up the usual way yielding a brown oil (2.49 g). The brown oil was purified by column chromatography. Flash silica (104 g) eluted with petroleum ether (600 ml) and increased to 5% diethyl diethyl ether/petroleum ether separated a clear pale green oil (1.50 g, 71% yield); m/z 210 (M+); (Found: C, 80.26; H, 4.91; S, 15.10. C14H10S requires: C, 80.00; H, 4.76; S, 15.24); H NMR (CDCl3), δ7.17 (dd, J=3.2, 5.6 Hz 1H), δ7.23 (dd, J=<1, 3.2 Hz, 1H), δ7.41 (dd, J=<1, 5.6 Hz, 1H), δ7.45 (d, J=4.8 Hz, 1H), δ7.47 (d, J=4.8 Hz, 1H) δ7.48 (d, J=8 Hz, 1H), δ7.55 (dd, J=<1, 8 Hz, 1H), δ7.83 (d, J=8 Hz, 1H), δ 7.88 (dd, J=3.2, 4.8 Hz, 1H), δ8.20 (dd, J=5.6, 4.8 Hz, 1H).

Sources & evidence

ORD record
ord-64fe978ced1343cb87863c0118a45e56
Source dataset
uspto-grants-1993_01
Patent number
US05180838

Reaction notes

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