N-bromobutanimide → 4-Bromo-7-methoxy-2-methoxymethylbenzofuran

HRID 2270119Notes

Reaction equation

HRID 2270119 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH2:12][O:13][CH3:14])=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[Br:15]N1C(=O)CCC1=O>C(#N)C>[Br:15][C:6]1[C:7]2[CH:8]=[C:9]([CH2:12][O:13][CH3:14])[O:10][C:11]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 184236407-Methoxy-2-methoxymethylbenzofuran

Product 1

HCID 184236394-Bromo-7-methoxy-2-methoxymethylbenzofuranYield 110.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 7-methoxy-2-methoxymethylbenzofuran (13.32 g) in acetonitrile (500 ml) was stirred at room temperature. N-bromosuccinimide (11.04 g) was added and stirring continued for 2 days after which the solvent was removed in vacuo. The resulting oil was partitioned between ethyl acetate (100 ml) and sodium metasulfite solution (50 ml), the organic extract washed with more sodium metasulfite solution (2×50 ml), followed by brine (50 ml). The organic layer was separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo to afford the title compound as a yellow oil (18.61 g).

Workup

  1. customafter which the solvent was removed in vacuo
  2. customThe resulting oil was partitioned between ethyl acetate (100 ml) and sodium metasulfite solution (50 ml)
  3. extractionthe organic extract
  4. washwashed with more sodium metasulfite solution (2×50 ml)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-539731bc6a884ee399288dab12ae68e7
Source dataset
uspto-grants-2001_12
Patent number
US06331556B2

Reaction notes

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