Methanol → 6-Bromo-thianthrene-2-carboxylic Acid Methyl Ester

HRID 33785Notes

Reaction equation

HRID 33785 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:3]=1[S:4][C:5]1[CH:6]=[CH:7][C:8]([C:16]([OH:18])=[O:17])=[CH:9][C:10]=1[S:11]2.OS(O)(=O)=O.[CH3:24]O>>[CH3:24][O:17][C:16]([C:8]1[CH:7]=[CH:6][C:5]2[S:4][C:3]3[C:12](=[CH:13][CH:14]=[CH:15][C:2]=3[Br:1])[S:11][C:10]=2[CH:9]=1)=[O:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22139422HCID 22139422, compound

Product 1

HCID 235745676-Bromo-thianthrene-2-carboxylic Acid Methyl Ester

Conditions

Temperature
80 °C

Procedure

To 6-bromo-thianthrene-2-carboxylic acid (9 g, 28 mmol) in methanol (180 ml) was slowly added conc. H2SO4 (5 ml). The milky white suspension was heated to 80° C. until all the solid had gone into solution (2 hrs). The suspension was concentrated in vacuo. Water (100 ml) was added and the organics were then extracted with dichloromethane (3×70 ml), dried over MgSO4 and evaporated in vacuo, yielding to a yellow solid. (4.48 g, 45%). 1HNMR (300 MHz, CDCl3): δH=3.94 (3H, s); 7.13 (1H, t), 7.44 (1H, dd), 7.54 (1H, dd) 7.61 (1H, d), 7.93 (1H, dd), 8.13 (1H, d).

Workup

  1. customhad gone into solution (2 hrs)
  2. concentrationThe suspension was concentrated in vacuo
  3. additionWater (100 ml) was added
  4. extractionthe organics were then extracted with dichloromethane (3×70 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customyielding to a yellow solid

Sources & evidence

ORD record
ord-79afa9279ea74543b768bce9cb70951f
Source dataset
uspto-grants-2008_09
Patent number
US07429660B2

Reaction notes

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