Water → HCID 14501061, compound

HRID 231131Notes

Reaction equation

HRID 231131 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]1([CH2:15][O:16][C:17]2[CH:25]=[CH:24][C:20]3[O:21][CH2:22][O:23][C:19]=3[CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>CN(C=O)C>[Br:1][C:25]1[C:17]([O:16][CH2:15][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:18][C:19]2[O:23][CH2:22][O:21][C:20]=2[CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 64552771,3-Benzodioxole, 5-(phenylmethoxy)-

Product 1

HCID 14501061HCID 14501061, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-bromosuccinimide (10.7 g, 0.06 mol) in dry DMF (70 ml) was added dropwise and with stirring a solution of 5-phenylmethoxy-1,3-benzodioxole (13.68, 0.06 mol) in dry DMF (80 ml). The resulting solution was stirred for 24 h at room temperature, poured into 300 ml of H2O and extracted with chloroform (3×70 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was recrystallized from absolute EtOH affording 17.4 g (94.5%) of 6-bromo-5-phenylmethoxy)-1,3-benzodioxole as white crystals mp 61.5°-62° C.; NMR (CDCl3, 90 MHz) δ 5.04 (S, 2H, CH2Ph), 5.91 (S, 2H, OCH2O), 6.56 (S, 1H, ArH), 6.99 (S, 1H, ArH), 7.14-7.63 (m, 5H, CH2Ph). Anal. calcd. for C14H11BrO3 : C, 54.75; H, 3.61; Br, 26.01. Found: C, 54.81; H, 3.64; Br, 25.68.

Workup

  1. extractionextracted with chloroform (3×70 ml)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from absolute EtOH affording 17.4 g (94.5%) of 6-bromo-5-phenylmethoxy)-1,3-benzodioxole as white crystals mp 61.5°-62° C.

Sources & evidence

ORD record
ord-a02d85a7cdf3418bbf43dcd2e0de7253
Source dataset
uspto-grants-1989_07
Patent number
US04845121

Reaction notes

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