Hydrochloric Acid → 2-Benzyloxy-5-chlorobenzeneboronic acid

HRID 1694693Notes

Reaction equation

HRID 1694693 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C[O:23][B:24](OC)[O:25]C.Cl>C(OCC)C>[CH2:15]([O:14][C:8]1[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=1[B:24]([OH:25])[OH:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 115511251-(Benzyloxy)-2-bromo-4-chlorobenzeneHCID 178418339Butyllithium2×

Product 1

HCID 41987402-Benzyloxy-5-chlorobenzeneboronic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of butyl lithium (1.6M in hexane) (50 ml) was added dropwise to a stirred solution of the product from step (i) (23 g) in diethylether (300 ml) at −70° C. After 1 h a further 18 ml of butyl lithium was added, left for 0.75 h, then trimethylborate (10 ml) added and the mixture warmed to RT and left for 16 h. 2M Hydrochloric acid (100 ml) was added, stirred for 1 h then the organic layer separated and extracted with aqueous sodium hydroxide solution. The basic layer was acidified with 2M hydrochloric acid solution, extracted with diethylether which was dried and evaporated under reduced pressure. The residue was triturated with iso-hexane and filtered. Yield 10.8 g

Workup

  1. waitleft for 16 h
  2. customthe organic layer separated
  3. extractionextracted with aqueous sodium hydroxide solution
  4. extractionextracted with diethylether which
  5. customwas dried
  6. customevaporated under reduced pressure
  7. customThe residue was triturated with iso-hexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-d4510e84f07d4702968317b1706b7cb4
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

Loading…