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

HRID 1695118Notes

Reaction equation

HRID 1695118 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-19b891c4ce244f6d8a558c50f1536b1d
Source dataset
uspto-grants-2012_04
Patent number
US08163727B2

Reaction notes

Loading…