Hydrochloric Acid → (2,5-Dichlorothiophen-3-yl)boronic acid

HRID 1740308Notes

Reaction equation

HRID 1740308 reaction equation
C([Li])CCC.Br[C:7]1[CH:11]=[C:10]([Cl:12])[S:9][C:8]=1[Cl:13].C([O:17][B:18](OC(C)C)[O:19]C(C)C)(C)C.Cl>CCCCCC.CCOCC>[Cl:13][C:8]1[S:9][C:10]([Cl:12])=[CH:11][C:7]=1[B:18]([OH:19])[OH:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 5219253-Bromo-2,5-dichlorothiopheneHCID 178418339Butyllithium

Product 1

HCID 21838136(2,5-Dichlorothiophen-3-yl)boronic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

n-Butyllithium in hexane (1.66M solution, 5.2 ml) was added dropwise to a solution of 3-bromo-2,5-dichlorothiophene (2.0 g) and triisopropoxyborane (2.4 ml) in ether (20.0 ml) at -75-65° C. for 10 minutes and the mixture was stirred at same temperature for 1 hour. The reaction mixture was poured onto 1N-hydrochloric acid (30 ml) and the mixture was extracted with ether. The separated extract layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give (2,5-dichlorothiophen-3-yl)-dihydroxyborane (1.13 g).

Workup

  1. extractionthe mixture was extracted with ether
  2. extractionThe separated extract layer
  3. washwas washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-196478ba56eb4e749b419d7dd4e2affc
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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