Water → 2-Bromo-4-formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid

HRID 1692630Notes

Reaction equation

HRID 1692630 reaction equation
[CH3:1][C:2]1[C:7]2[C:8]([O:10][C:11]3[C:12]([CH3:23])=[C:13]([O:21][CH3:22])[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[C:16]=3[O:17][C:6]=2[C:5]([CH:24]=[O:25])=[C:4]([OH:26])[CH:3]=1)=[O:9].[Br:27]Br.O>C(O)(=O)C>[Br:27][C:3]1[C:4]([OH:26])=[C:5]([CH:24]=[O:25])[C:6]2[O:17][C:16]3[C:15]([C:18]([OH:20])=[O:19])=[CH:14][C:13]([O:21][CH3:22])=[C:12]([CH3:23])[C:11]=3[O:10][C:8](=[O:9])[C:7]=2[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 23725Psoromic AcidHCID 24408Bromine

Product 1

HCID 873372362-Bromo-4-formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of psoromic acid (1 mmol) in glacial acetic acid (5 ml) was dropwise added a solution of bromine (3 mmol, 0.15 ml) in glacial acetic acid (3 ml). After stirring at room temperature for several hours, the redbrown reaction mixture was poured into water (50 ml), extracted with ethyl acetate (100 ml), dried with MgSO4, filtered, and evaporated by a rotatory evaporator to give a redbrown solid.

Workup

  1. customthe redbrown reaction mixture
  2. extractionextracted with ethyl acetate (100 ml)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated by a rotatory evaporator
  6. customto give a redbrown solid

Sources & evidence

ORD record
ord-396a417942ea4d689690c15a3d9da7dc
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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