Hydrochloric Acid → 6-Bromo-benzo[b]thiophene

HRID 572401Notes

Reaction equation

HRID 572401 reaction equation
C1CCN2C(=NCCC2)CC1.[Br:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[C:19](C(O)=O)[S:18][C:17]=2[CH:24]=1.C(OCC)(=O)C.Cl>CC(N(C)C)=O.CCCCCC>[Br:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[CH:19][S:18][C:17]=2[CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 135679806-Bromo-1-benzothiophene-2-carboxylic acid

Product 1

HCID 127444006-Bromo-benzo[b]thiopheneYield 78%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
200 °C

Procedure

DBU (1.21 g, 8.00 mmol) was added to a stirred solution of 6-bromo-benzo[b]thiophene-2-carboxylic acid (I-25b: 2.4 g, 8.85 mmol) in DMA (4 mL) at room temperature and the resulting mixture was heated in microwave at 200° C. for 1 hour. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mixture was acidified with 1N HCl and extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography on silica gel (100% hexane) to afford 320 mg of the product (78% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by column chromatography on silica gel (100% hexane)

Sources & evidence

ORD record
ord-267b855712a64cfcac4df832c0d35554
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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