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Hydrogen Bromide → 5-Hydroxy-6-methoxy-4-nitro-isobenzofuran-1,3-dione

HRID 1881209
Notes
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Reaction equation

HRID 1881209 reaction equation
C[O:2][C:3]1[C:4]([N+:16]([O-:18])=[O:17])=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[O:7][C:6]2=[O:15].Br>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(O)(=O)C>[OH:2][C:3]1[C:4]([N+:16]([O-:18])=[O:17])=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[O:7][C:6]2=[O:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 866334445,6-Dimethoxy-4-nitro-isobenzofuran-1,3-dione

Product 1

HCID 866334455-Hydroxy-6-methoxy-4-nitro-isobenzofuran-1,3-dione

Reagents, catalysts & solvents 2

HCID 165294Benzyltriethylammonium bromideCatalystHCID 176Acetic AcidSolvent

Procedure

5,6-Dimethoxy-4-nitro-isobenzofuran-1,3-dione (346 mg), 48% hydrogen bromide (1.5 ml), Acetic acid (15 ml) and benzyl triethylammonium bromide (37 mg) were heated at 140° C. for 3 hours. The acetic acid and water was removed in vacuo. The remainder was filtered through silica gel using a mixture of toluene, ethyl acetate and methanol (8:1:1) as eluent. Appropriate fractions were collected and evaporated.

Workup

  1. customThe acetic acid and water was removed in vacuo
  2. filtrationThe remainder was filtered through silica gel using
  3. additiona mixture of toluene, ethyl acetate and methanol (8:1:1) as eluent
  4. customAppropriate fractions were collected
  5. customevaporated

Sources & evidence

ORD record
ord-4a19ad6978ea4769a64bb0740041eb0d
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318785B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes