Bromine → HCID 821949, compound

HRID 746623Notes

Reaction equation

HRID 746623 reaction equation
[S:1]1[C:5]([CH2:6][CH2:7][OH:8])=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[Br:13]Br.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Br:13][C:4]1[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=2[S:1][C:5]=1[CH2:6][CH2:7][OH:8]

Participants

5

Reactant 3

HCID 24408BromineHCID 280609Benzo(b)thiophene-2-ethanolHCID 516892Sodium Bicarbonate

Product 1

HCID 821949HCID 821949, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a cooled solution (0° C.) of 2-benzo[b]thiophen-2-yl-ethanol (5 g, 28.1 mmol) in CHCl3 (30 mL), bromine (1.73 mL, 33.7 mmol) was added dropwise. The reaction was stirred overnight while gradually being warmed to room temperature. Saturated NaHCO3 was added and the organic layer was separated. The aqueous layer was subsequently extracted with dichloromethane and the combined organic layers were dried (Na2SO4) and concentrated in vacuo to afford 2-(3-bromo-benzo[b]thiophen-2-yl)-ethanol in quantitative yield.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was subsequently extracted with dichloromethane
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b336e57dc5e410db07b2ddcb4028c5a
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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