Metaperiodic acid → HCID 68226869, compound

HRID 1952638Notes

Reaction equation

HRID 1952638 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:11][OH:12])=[CH:8][C:9]=1[Br:10])=[O:4].I(O)(=O)(=O)=[O:14]>CC#N.CCOC(C)=O.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]([OH:14])=[O:12])=[CH:8][C:9]=1[Br:10])=[O:4]

Participants

6

Reactant 2

HCID 65185Metaperiodic acidHCID 68226825HCID 68226825, compound

Product 1

HCID 68226869HCID 68226869, compoundYield 101.3%

Reagents, catalysts & solvents 3

HCID 178418287HCID 178418287, compoundCatalystHCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-Bromo-5-hydroxymethyl-thiophene-2-carboxylic acid methyl ester (0.19 g, 0.76 mmol) and Periodic Acid (0.38 g, 1.66 mmol) in MeCN (10 ml) was stirred for 30 min A solution of PCC (0.010 g, 0.015 mmol) in MeCN (0.2 ml) was added. After 2 h, the reaction mixture was diluted with EtOAc (50 ml), washed with sodium sulfite, brine, dried over sodium sulfate, filtered and evaporated. Isolate 0.204 g (100%) of yellow solid product.

Workup

  1. additionwas added
  2. washwashed with sodium sulfite, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6bd8f5dfb7474233be0d4a9540ca2d9d
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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