Chlorosuccinimide → 7-Chloro-2,3-dihydrobenzo[b][1,4]dioxin-6-ol

HRID 2385111Notes

Reaction equation

HRID 2385111 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.[Cl:12]N1C(=O)CCC1=O>CN(C)C=O>[Cl:12][C:11]1[C:2]([OH:1])=[CH:3][C:4]2[O:9][CH2:8][CH2:7][O:6][C:5]=2[CH:10]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 91152732,3-Dihydro-1,4-benzodioxin-6-ol

Product 1

HCID 673794857-Chloro-2,3-dihydrobenzo[b][1,4]dioxin-6-olYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-hydroxy-1,4-benzodioxane (1.52 g, 10 mmol) in N,N-dimethylformamide (10 mL) was added N-chlorosuccinimide (1.33 g, 10 mmol) at ambient temperature. The solution was stirred at ambient temperature for 16 h and concentrated in vacuo. The residue was purified by column chromatography and eluted with a 15% to 30% gradient of ethyl acetate in hexanes to afford 7-chloro-2,3-dihydrobenzo[b][1,4]dioxin-6-ol (1.79 g, 96%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.02 (s, 1H), 6.83 (s, 1H), 6.56 (s, 1H), 4.27-4.16 (m, 4H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography
  3. washeluted with a 15% to 30% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-546682b84cda4c6dae854bdca8e5b4ad
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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