Boron tribromide → HCID 22413374, compound

HRID 1721592Notes

Reaction equation

HRID 1721592 reaction equation
[O:1]1[C:5]2[C:6]([CH:10]3[C:16]4[CH:17]=[CH:18][C:19]([O:23]C)=[C:20]([O:21]C)[C:15]=4[CH2:14][CH2:13][N:12]([CH3:25])[CH2:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.B(Br)(Br)Br>ClCCl>[O:1]1[C:5]2[C:6]([CH:10]3[C:16]4[CH:17]=[CH:18][C:19]([OH:23])=[C:20]([OH:21])[C:15]=4[CH2:14][CH2:13][N:12]([CH3:25])[CH2:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22413366HCID 22413366, compound

Product 1

HCID 22413374HCID 22413374, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-60 °C

Procedure

1.10 g (0.0033 mol) 1 -(benzofuran-7-yl)-6,7-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1-H-3-benzazepine was dissolved in 25 ml dry dichloromethane. The solution was cooled to -60° C. and 0.93 (0.0098 mol) boron tribromide was slowly added. The reaction mixture was stirred at -60° C. for 15 min., allowed to warm up to 0° C. and stirred for 1 h. Evaporation in vacuo left a brown residue, which was redissolved in dichloromethane. The solution was stirred in an ice bath and 5 ml methanol was added dropwise. The solution was again concentrated in vacuo, the residue was dissolved in 6N HCl and refluxed for 30 min. Then pH was adjusted to 8 with 2N NaOH-solution and the product extracted with ethylacetate. The organic layer was washed with water and brine and concentrated in vacuo. 1-(Benzofuran-7-yl)-6,7-dihydroxy-3-methyl-2,3,4,5,-tetrahydro-1H-3-benzazepine was obtained as an offwhite powder.

Workup

  1. temperatureto warm up to 0° C.
  2. stirringstirred for 1 h
  3. customEvaporation in vacuo
  4. waitleft a brown residue, which
  5. dissolutionwas redissolved in dichloromethane
  6. stirringThe solution was stirred in an ice bath
  7. addition5 ml methanol was added dropwise
  8. concentrationThe solution was again concentrated in vacuo
  9. dissolutionthe residue was dissolved in 6N HCl
  10. temperaturerefluxed for 30 min
  11. extractionthe product extracted with ethylacetate
  12. washThe organic layer was washed with water and brine
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8c0532d3d4544d5b123502752a83ca6
Source dataset
uspto-grants-1996_04
Patent number
US05512562

Reaction notes

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