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

HRID 723532Notes

Reaction equation

HRID 723532 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]Br>ClCCl>[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

4

Reactant 2

HCID 24408BromineHCID 891481,4-Benzodioxan-6-ylamine

Product 1

HCID 49832297-bromo-2,3-dihydro-1,4-benzodioxin-6-amineYield 30.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,3-dihydro-benzo[1,4]dioxin-6-ylamine (32 g, 212 mmol) in dichloromethane (1 liter) was treated with a solution of bromine (10.8 ml, 212 mmol) in dichloromethane (100 ml) at 0° C. After the addition the mixture was stirred at room temperature for 1 hour then washed with saturated aqueous sodium bicarbonate solution containing a small amount of sodium sulphite. The organic organic extract was dried and evaporated affording an oil that was chromatographed on silica gel eluting with dichloromethane to afford an oil (14.8 g, 30%).

Workup

  1. additionAfter the addition the mixture
  2. washthen washed with saturated aqueous sodium bicarbonate solution
  3. additioncontaining a small amount of sodium sulphite
  4. extractionThe organic organic extract
  5. customwas dried
  6. customevaporated
  7. customaffording an oil that
  8. customwas chromatographed on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-ef8ab915944c458ab953ba7c763bae72
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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