Boron tribromide → HCID 68516960, compound

HRID 732776Notes

Reaction equation

Cl.C[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([O:14][C:15]1[CH:29]=[CH:28][C:18]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:17][CH:16]=1)=[C:9]([C:30]1[CH:35]=[CH:34][C:33]([S:36][CH3:37])=[CH:32][C:31]=1[CH3:38])[CH:8]=[CH:7]2.B(Br)(Br)Br>ClCCl>[CH3:38][C:31]1[CH:32]=[C:33]([S:36][CH3:37])[CH:34]=[CH:35][C:30]=1[C:9]1[C:10]([O:14][C:15]2[CH:29]=[CH:28][C:18]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:17][CH:16]=2)=[C:11]2[C:6](=[CH:7][CH:8]=1)[CH:5]=[C:4]([OH:3])[CH:13]=[CH:12]2

Participants

Conditions

Temperature: 5 °C

Procedure

Dissolve 1-(2-{4-[6-methoxy-2-(2-methyl-4-methylsulfanyl-phenyl)-naphthalen-1-yloxy]-phenoxy}-ethyl)-piperidine hydrochloride (331 mg, 0.603 mmol) in dichloromethane (15 mL) and cool to 5° C. Add BBr3 (285 μL, 3.02 mmol) to the light suspension over 5 minutes. Quench the reaction after 1 hour with saturated aqueous NaHCO3 (15 mL). Separate the layers and extract the aqueous layer with dichloromethane (2×10 mL). Pour the solution onto a SiO2 plug (20 g) and elute with methanol in dichloromethane (5 to 15%). Concentrate the fractions in vacuo to give 301 mg of the title compound (100%): mass spectrum (ion spray) m/z=500.3 (M+H).

Workup

customQuench
customthe reaction after 1 hour with saturated aqueous NaHCO3 (15 mL)
customSeparate the layers
extractionextract the aqueous layer with dichloromethane (2×10 mL)
additionPour the solution onto a SiO2 plug (20 g)
washelute with methanol in dichloromethane (5 to 15%)
concentrationConcentrate the fractions in vacuo

Sources & evidence

ORD record: ord-a819ef9dde2d4755b5a1de9e1c2e6536
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585977B2

Reaction notes

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