Boron tribromide → 6-(1-Benzyl-3-pentyl-1H-indol-2-yl)-2-naphthol

HRID 2252959Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[C:9]1[C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([O:32]C)[CH:28]=2)[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[C:9]1[C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[CH:28]=[C:27]([OH:32])[CH:26]=[CH:25]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

In such processes, a solution of 1-benzyl-2-(6-methoxy-naphthalen-2-yl)-3-pentyl-1H-indole in methylene chloride generally is treated with 0.75 equivalents of boron tribromide in methylene chloride at 0° C., the resulting mixture is slowly heated to 25° C., and the reaction is quenched with a 5% solution of sodium hydroxide in water. The organic and aqueous layers are separated, and the organic layer is replaced with toluene. Heptane is added to the solution and the product is crystallized at 0° C. to produce 85% to 90% of 6-(1-benzyl-3-pentyl-1H-indol-2-yl) -naphthalen-2-ol.

Workup

customthe reaction is quenched with a 5% solution of sodium hydroxide in water
customThe organic and aqueous layers are separated
additionHeptane is added to the solution
customthe product is crystallized at 0° C.

Sources & evidence

ORD record: ord-d8f46f253ddf436c971c0977698702ef
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323483B2

Reaction notes

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