N-bromobutanimide → 7-bromo-2,3-dihydro-1,4-benzodioxin-6-amine

HRID 1782015Notes

Reaction equation

HRID 1782015 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[Br:12]N1C(=O)CCC1=O>O1CCCC1.S(=O)(=O)(O)O>[Br:12][C:8]1[C:9]([NH2:11])=[CH:10][C:5]2[O:4][CH2:3][CH2:2][O:1][C:6]=2[CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 891481,4-Benzodioxan-6-ylamine

Product 1

HCID 49832297-bromo-2,3-dihydro-1,4-benzodioxin-6-amineYield 93%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,3-dihydro-benzo[1,4]dioxin-6-ylamine (1 g, 6.6 mmol) in tetrahydrofuran (15 ml) was cooled to −78 deg C. then treated with 1 drop of concentrated sulphuric acid followed by N-bromosuccinimide (1.2 g, 6.6 mmol). The mixture was allowed to warm to room temperature over 1 hour then evaporated. The residue was dissolved in ether, washed with water then brine, dried and evaporated to afford an oil (1.4 g, 93%).

Workup

  1. customthen evaporated
  2. dissolutionThe residue was dissolved in ether
  3. washwashed with water
  4. dry with materialbrine, dried
  5. customevaporated

Sources & evidence

ORD record
ord-5389309b1db84247bd8965dc569dee38
Source dataset
uspto-grants-2009_03
Patent number
US07498326B2

Reaction notes

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