Hydrochloric Acid → (2-Ethylthiophenyl)boronic acid

HRID 496791Notes

Reaction equation

HRID 496791 reaction equation
[B:1](OC(C)C)([O:6]C(C)C)[O:2]C(C)C.Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21][CH2:22][CH3:23].[Li]CCCC.CCCCCC.Cl>C(OCC)(=O)C>[CH2:22]([S:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[B:1]([OH:6])[OH:2])[CH3:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 130827251-Bromo-2-(ethylsulfanyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 3785655(2-Ethylthiophenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

9.5 g (50 mmol) of triisopropyl borate are added to a solution of 10.9 g (50.0 mmol) of 1-bromo-2-ethylsulfanylbenzene kept at −70° C. 33.3 ml of a 15% solution of BuLi in hexane (55 mmol) are then added. The mixture is stirred at −70° C. for a further 30 minutes, then 1 N hydrochloric acid and ethyl acetate are added. The organic phase is separated off, dried and evaporated. The residue is taken up in diethyl ether and filtered. A colourless solid is obtained; FAB 182

Workup

  1. customkept at −70° C
  2. customThe organic phase is separated off
  3. customdried
  4. customevaporated
  5. filtrationfiltered
  6. customA colourless solid is obtained

Sources & evidence

ORD record
ord-8215473de7e84f9db4a581d52f40e108
Source dataset
uspto-grants-2005_09
Patent number
US06946489B2

Reaction notes

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