2-Bromonaphthalene → HCID 454756, compound

HRID 727932Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.BrC1C=CC2C(=CC=CC=2)C=1>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:15]=1

Participants

Reactant 2

HCID 113722-Bromonaphthalene

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

Product 1

HCID 454756HCID 454756, compound

Procedure

The 2-(2-thienyl)-naphthalene was prepared in the same manner as for the 1-thienyl-naphthalene derivative, with the Grignard being added to 2-bromonaphthalene (2.07 g, 0.01 m). After workup, a brown solid (2.39 g) was isolated. Column chromatography yielded 2-bromonaphthalene (630 mg) and a white crystalline solid (1.13 g, 73% yield based on recovered starting material); m.p. 103°-104° C.; m/z 210 (M+); (Found: C, 79.75; H, 4,80; S, 15.09. C14H10S requires C, 80.0; H, 4.76; S, 15.24); H NMR (CDCl3); δ7.17 (dd, J=5.6, 3.5 Hz, 1H), δ7.30 (dd, J=<1, 5.6 Hz, 1H), δ7.42 (dd, J=<1, 5 Hz 1H), δ7.45 (dd, J=<1, 7 Hz, 1H), δ7.46 (dd, J=1, 4.0 Hz, 1H), δ 7.73 (dd, J=1, 8.0 Hz, 1H), δ7.79 (dd, J=1, 8 Hz, 1H), δ7.81 (s, 1H), δ7.83 (s, 1H), δ5.803 (d, <1, Hz, 1H).

Sources & evidence

ORD record: ord-67313686d888431b94a8bb05f660f1a4
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05045563

Reaction notes

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