Dimethyl Sulfide → 8-Bromo-2-chloro-5,6,11,12-tetrahydro-dibenzo[b,f]azocine-12-ol

HRID 2220200Notes

Reaction equation

[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[CH2:6][C:7](=[O:18])[C:8]3[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:9]=3[NH:10][C:11](=O)[C:4]=2[CH:3]=1.CSC>C1COCC1>[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[CH2:6][CH:7]([OH:18])[C:8]3[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:9]=3[NH:10][CH2:11][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 8-Bromo-2-chloro-5H,11H-dibenzo[b,f]azocine-6-12-dione (2.0 g, 5.7 mmole) in THF (20 mL) was added a 2.0M solution of BH3.DMS in THF (6.9 mL, 14.3 mmole). The reaction mixture was heated to 70° C. for 6 hours. The reaction was quenched by slow addition of methanol and stirred at room temperature for 40 minutes. The residue obtained after concentration was triturated with methanol, filtered and dried in vacuo to give 8-Bromo-2-chloro-5,6,11,12-tetrahydro-dibenzo[b,f]azocine-12-ol (0.85 g, 44%). HPLC Rt=3.31 min. m/z=338 (M+H+).

Workup

customThe reaction was quenched by slow addition of methanol
customThe residue obtained
concentrationafter concentration
customwas triturated with methanol
filtrationfiltered
customdried in vacuo

Sources & evidence

ORD record: ord-eb5861b5033845f9ab47dd0232a4d959
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417040B2

Reaction notes

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