Bromine → N-(8-Bromobenzo[1,4]dioxan-5-yl)-acetamide

HRID 751046

Reaction equation

HRID 751046 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([NH:11][C:12](=[O:14])[CH3:13])[C:5]=2[O:4][CH2:3][CH2:2]1.[Br:15]Br>C(Cl)(Cl)Cl>[Br:15][C:7]1[C:6]2[O:1][CH2:2][CH2:3][O:4][C:5]=2[C:10]([NH:11][C:12](=[O:14])[CH3:13])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 658593N-(2,3-dihydro-1,4-benzodioxin-5-yl)acetamide

Product 1

HCID 23269228N-(8-Bromobenzo[1,4]dioxan-5-yl)-acetamideYield 86.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of compound 8C (0.80 g, 4.15 mmol) in chloroform (2.4 mL) cooled to −20° C. was slowly added a solution of bromine (0.22 mL, 4.35 mmol) in chloroform (1 mL) so that the reaction temperature was maintained below −10° C. The reaction was stirred at 0° C. for 5 min, and then quenched immediately with water. The mixture was extracted with CH2Cl2 (3×), the combined extracts washed with saturated NaHCO3, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with CH2Cl2 to afford the title compound (0.98 g).

Workup

  1. temperaturewas maintained below −10° C
  2. customquenched immediately with water
  3. extractionThe mixture was extracted with CH2Cl2 (3×)
  4. washthe combined extracts washed with saturated NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed (silica gel)
  9. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-a0270390e7904d468a99460862bd2505
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Linked notes

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