Acetic Acid → 5-(3-bromopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 1046726Notes

Reaction equation

[CH:1]1([C:4]2(O)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][CH2:7][C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]2=3)[CH2:3][CH2:2]1.C(O)(=O)C.[BrH:24]>C(Cl)Cl>[Br:24][CH2:3][CH2:2][CH:1]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2

Participants

Conditions

Temperature: 10 °C

Procedure

In a 100-mL round bottom flask, 5-cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ol (0.130 g, 0.0006 mol) was added with 1 mL acetic acid. The solid was allowed to dissolve at which point the reaction mixture was chilled to 10° C. Then a solution of 33% hydrobromic acid (0.5 mL hydrobromic acid and 0.5 mL acetic acid; total 1 mL) was added to the flask. The reaction was allowed to stir for an additional 30 min. while reaction progress was monitored by HPLC. Then the reaction mixture was transferred to a separatory funnel and DCM (100 mL) added. The organic layer collected and washed with H2O (1×100 mL) and dried over Na2SO4 for 2 hrs. The resulting product was purified by flash column chromatography on silica gel using MeOH/DCM (Biotage 25M column). The product was confirmed by 1H NMR and LC/MS. (Yield ˜62%)

Workup

dissolutionto dissolve at which
customThen the reaction mixture was transferred to a separatory funnel
customThe organic layer collected
washwashed with H2O (1×100 mL)
dry with materialdried over Na2SO4 for 2 hrs
customThe resulting product was purified by flash column chromatography on silica gel

Sources & evidence

ORD record: ord-838e7048a4274a1d9e638dd06a733fed
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569380B2

Reaction notes

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