Iodine → 6-Hydroxy-5-methoxybenzo[b]thiophene-2-carboxylic acid

HRID 1881179Notes

Reaction equation

HRID 1881179 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[C:16](\[SH:20])/[C:17]([OH:19])=[O:18])=[CH:11][C:10]=1[O:21][CH3:22])C1C=CC=CC=1.II.O.S(=O)(O)[O-].[Na+]>O1CCCC1>[OH:8][C:9]1[C:10]([O:21][CH3:22])=[CH:11][C:12]2[CH:15]=[C:16]([C:17]([OH:19])=[O:18])[S:20][C:13]=2[CH:14]=1

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 23665763Sodium BisulfiteHCID 86633439HCID 86633439, compound

Product 1

HCID 212834786-Hydroxy-5-methoxybenzo[b]thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Z)-3-(4-Benzyloxy-3-methoxy-phenyl)-2-mercapto-acrylic acid (21 g) and iodine (21 g) in tetrahydrofuran (300 ml) was stirred in 60° C. for 15 hours. Then it was poured into water (1 l) and 120 g sodium bisulfite was added. The product was extracted into ethylacetate and then it extracted into sodium bicarbonate. The water phase was acified by concentrated hydrochloric acid and stirred in room temperature for one hour. The solid was filtered, washed with water and dried under vacuum.

Workup

  1. additionwas added
  2. extractionThe product was extracted into ethylacetate
  3. extractionit extracted into sodium bicarbonate
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-a9c083e14f3143af8b40c21c965c01a5
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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