Hydrogen Bromide → HCID 66986851, compound

HRID 556124Notes

Reaction equation

HRID 556124 reaction equation
[C:1]1([C:7]2[CH:24]=[CH:23][C:10]3[C:11]([CH:21]=[CH2:22])(O)[C:12]4[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=4[CH2:14][CH2:15][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BrH:25]>C(O)(=O)C>[C:1]1([C:7]2[CH:24]=[CH:23][C:10]3[C:11](=[CH:21][CH2:22][Br:25])[C:12]4[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=4[CH2:14][CH2:15][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 19261789HCID 19261789, compound

Product 1

HCID 66986851HCID 66986851, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A suspension of the above alcohol (1.56 g, 5.06 mmol) in acetic acid (15 mL) was stirred and treated at 15° C. with 15% solution of hydrogen bromide in acetic acid (10 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 (75 g, benzene). The benzene solutions were evaporated in vacuo to yield 1.58 g (87.5%) of 2-phenyl-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 (75 g, benzene)
  5. customThe benzene solutions were evaporated in vacuo

Sources & evidence

ORD record
ord-cfe29016e6dc4247a3077f3e66b07372
Source dataset
uspto-grants-2011_11
Patent number
US08053598B2

Reaction notes

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