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

HRID 250281Notes

Reaction equation

HRID 250281 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8](C(O)=O)[S:7][C:6]=2[CH:13]=1.Cl>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 135679806-Bromo-1-benzothiophene-2-carboxylic acid

Product 1

HCID 127444006-Bromo-benzo[b]thiopheneYield 62.7%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
195 °C

Procedure

Copper powder (100 g, 1.57 mol) is added to a solution of 6-bromo-benzo[b]-thiophene-2-carboxylic acid (1.04 Kg, 4.04 mol) in quinoline (2.5 L) at room temperature. The reaction mixture is heated to reflux (195° C.) for 10 h. The reaction mixture is cooled to room temperature and poured onto ice (2.5 Kg). Concentrated HCl (2.5 L) is added while stirring the resulting mass for 1 h. The reaction mixture is extracted with hexane (4×3 L) and washed with dilute HCl (1×2 L), aqueous bicarbonate (1×5 L), and brine solution (1×5 L). The layers are separated and the organic layer is dried over sodium sulfate and concentrated to give the title compound (0.54 Kg, 62%) as a light yellow solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureThe reaction mixture is cooled to room temperature
  3. additionpoured onto ice (2.5 Kg)
  4. extractionThe reaction mixture is extracted with hexane (4×3 L)
  5. washwashed with dilute HCl (1×2 L), aqueous bicarbonate (1×5 L), and brine solution (1×5 L)
  6. customThe layers are separated
  7. dry with materialthe organic layer is dried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-34b07e5fdd7b4d1b946a61307ae14048
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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