Hydrogen Bromide → HCID 66986789, compound

HRID 556122Notes

Reaction equation

HRID 556122 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:16]=[CH2:17])(O)[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.[BrH:20]>C(O)(=O)C>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[CH:16][CH2:17][Br:20])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 19261783HCID 19261783, compound

Product 1

HCID 66986789HCID 66986789, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A suspension of the above alcohol (1.1 g, 3.49 mmol) in acetic acid (10 mL) was stirred and treated at 15° C. with 15% solution of hydrogen bromide in acetic acid (7 mL) over 15 min. The mixture was stirred at 15° C. for 30 min and then at laboratory temperature for 1.5 h and evaporated in vacuo. The rest of acetic acid was removed by addition of 40 mL xylene and evaporation in vacuo and the residue was chromatographed in a short column of silica gel Fluka 60 (50 g, benzene). The benzene solutions were evaporated in vacuo to yield 1.25 g (95%) of 2-bromo-5-(2-bromo-ethylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene.

Workup

  1. stirringThe mixture was stirred at 15° C. for 30 min
  2. customevaporated in vacuo
  3. customThe rest of acetic acid was removed by addition of 40 mL xylene and evaporation in vacuo
  4. customthe residue was chromatographed in a short column of silica gel Fluka 60 (50 g, benzene)
  5. customThe benzene solutions were evaporated in vacuo

Sources & evidence

ORD record
ord-0371f3f1645148b5907fda16a2a04e9f
Source dataset
uspto-grants-2011_11
Patent number
US08053598B2

Reaction notes

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