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

HRID 970389Notes

Reaction equation

HRID 970389 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 litre) 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 extract was dried and evaporated to 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 extract
  5. customwas dried
  6. customevaporated to an oil that
  7. customwas chromatographed on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-b0528b41507247069c02e94313101cc8
Source dataset
uspto-grants-2007_12
Patent number
US07312212B2

Reaction notes

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