Hydrochloric Acid → 3-Chloro-4-(methylthio)phenylboronic acid

HRID 1023766Notes

Reaction equation

HRID 1023766 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[C:9]([Cl:15])[CH:8]=1.C([O:19][B:20](OC(C)C)[O:21]C(C)C)(C)C.Cl>C1COCC1>[Cl:15][C:9]1[CH:8]=[C:7]([B:20]([OH:21])[OH:19])[CH:12]=[CH:11][C:10]=1[S:13][CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 573461311-Bromo-3-chloro-4-(methylthio)benzeneHCID 178418339Butyllithium

Product 1

HCID 686641083-Chloro-4-(methylthio)phenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Butyl lithium (15 ml, 1.9M in hexanes) was added over 40 min to a solution of the product from step b) (6.82 g) and triisopropylborate (8.0 ml) in THF (30 ml) at −78° C. and stirred for a further 1 h. 2M HCl (20 ml) was added, the mixture was warmed to 20° C. and extracted with ether (three times). The organic extracts were dried (MgSO4), evaporated and purified by chromatography (silica, petrol-ether as eluent) to give the sub-title compound (1.82 g).

Workup

  1. extractionextracted with ether (three times)
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. customevaporated
  4. custompurified by chromatography (silica, petrol-ether as eluent)

Sources & evidence

ORD record
ord-cacb818b85584acf8f51a6b34ef1cf40
Source dataset
uspto-grants-2014_05
Patent number
US08722741B2

Reaction notes

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