Bicarbonate Ion → HCID 58390811, compound

HRID 1015666Notes

Reaction equation

HRID 1015666 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].OS(O)(=O)=O.[I:12][C:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[S:15][C:14]=1[C:24]([OH:26])=[O:25].[C:27](O)([CH3:30])([CH3:29])[CH3:28].C(=O)(O)[O-]>ClCCl>[C:27]([O:25][C:24]([C:14]1[S:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:17][C:13]=1[I:12])=[O:26])([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 5

HCID 769Bicarbonate IonHCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 22496314HCID 22496314, compound

Product 1

HCID 58390811HCID 58390811, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of magnesium sulfate (4.61 g, 38.32 mmol) in dichloromethane (37 ml) at 21° C., under N2, was treated with conc H2SO4 (510 μl, 9.58 mmol). After 15 min solid 3-Iodo-5-phenyl-thiophene-2-carboxylic acid (3.7 g, 9.58 mmol) was added followed by t-butanol (4.55 ml, 47.9 mmol) and the flask was stoppered and left over-night for 19.5 h. The reaction mixture was treated with saturated bicarbonate aqueous solution, and filtered. The solid was washed with CH2Cl2 and the filtrate dried and concentrated to an oil. The crude material was purified by flash chromatography using Hexane/CH2Cl2 (3:1) as eluent to give 1.63 g (44%) of 3-Iodo-5-phenyl-thiophene-2-carboxylic acid tert-butyl ester as a colorless solid. NMR 1H (CDCl3, 400 MHz) 7.61-7.59 (m, 2H); 7.43-7.35 (m, 3H), 7.25 (s, 1H), 1.60 (bs, 9H).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with CH2Cl2
  3. customthe filtrate dried
  4. concentrationconcentrated to an oil
  5. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-12aa09f0d32b48f3a85891be4eb72063
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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