tert-Butyl methyl ether → HCID 58591579, compound

HRID 746606Notes

Reaction equation

HRID 746606 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][C:5]1[S:9][C:8]2[CH:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:7]=2[CH:6]=1.[Br:16]Br.CC(OC)(C)C>CC(O)=O>[Br:16][C:6]1[C:7]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:8]=2[S:9][C:5]=1[CH2:4][CH2:3][N:2]([CH3:1])[CH3:15]

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 24408BromineHCID 58591573HCID 58591573, compound

Product 1

HCID 58591579HCID 58591579, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of dimethyl-[2-(6-methyl-benzo[b]thiophen-2-yl)-ethyl]-amine (1.05 g, 4.78 mmol) in HOAc (5 mL) at 0° C., bromine was added slowly. The mixture was stirred overnight while it was allowed to slowly reach room temperature. MTBE (6 mL) was added and the solid was filtered, washed with MTBE and dried under vacuum. It was taken up in dichloromethane, washed with sat. NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo to give 1.1 g of [2-(3-bromo-6-methyl-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amine (77% yield).

Workup

  1. customwas allowed to slowly reach room temperature
  2. filtrationthe solid was filtered
  3. washwashed with MTBE
  4. customdried under vacuum
  5. washwashed with sat. NaHCO3 and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39c842fd9f2e49b893c988575918e8e3
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

Loading…