2-(Bromomethyl)-5-nitro-1-benzofuran → Phthalimide

HRID 363001Notes

Reaction equation

HRID 363001 reaction equation
BrCC1OC2C=CC([N+]([O-])=O)=CC=2C=1.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.[K]>C(#N)C.C1OCCOCCOCCOCCOCCOC1>[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12

Participants

5

Reactant 2

HCID 114141792-(Bromomethyl)-5-nitro-1-benzofuranHCID 24194345Phthalimide potassium salt

Product 1

HCID 6809PhthalimideYield 108.7%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of the above 2-bromomethyl-5-nitrobenzofuran (1.57 g, 6.13 mmol), potassium phthalimide (1.70 g, 9.19 mmol), and 18-crown-6 (0.161 g, 0.61 mmol) was stirred in acetonitrile (15 mL) overnight at room temperature. The solvent was removed by vacuum, and the residue was partitioned between ethyl acetate and brine. The organic phase was washed with 0.1N sodium hydroxide (2×50 mL) then brine (2×50 mL), dried (MgSO4) and concentrated to afford an off-white solid. The crude product was triturated with cold ethyl acetate/diethyl ether/hexane to afford 1.47 g (74%) of phthalimide adduct as a white solid: 1H NMR (DMSO-d6): δ 8.55 (d, 1H), 8.17 (dd, 1H), 7.88 (m, 4H), 7.75 (d, 1H), 5.00 (s, 2H).

Workup

  1. customThe solvent was removed by vacuum
  2. customthe residue was partitioned between ethyl acetate and brine
  3. washThe organic phase was washed with 0.1N sodium hydroxide (2×50 mL)
  4. dry with materialbrine (2×50 mL), dried (MgSO4)
  5. concentrationconcentrated
  6. customto afford an off-white solid
  7. customThe crude product was triturated with cold ethyl acetate/diethyl ether/hexane

Sources & evidence

ORD record
ord-81fb5ade98b0439aba009a7c89bcefe1
Source dataset
uspto-grants-1999_02
Patent number
US05872139

Reaction notes

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