Water → 4-Benzyloxy-phenylboronic acid

HRID 1857650Notes

Reaction equation

HRID 1857650 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].C([O:8][B:9](OCC)[O:10]CC)C.O.S(=O)(=O)(O)O.[CH2:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[C:28]([O:31][CH2:32][CH3:33])(=O)C>O1CCCC1>[C:22]1([CH2:28][O:31][C:32]2[CH:33]=[CH:4][C:3]([B:9]([OH:10])[OH:8])=[CH:2][CH:1]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 9009Triethyl borateHCID 21867204Cyclohexane ethylacetateHCID 178418339Butyllithium

Product 1

HCID 27343144-Benzyloxy-phenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

143 ml of a solution of n-Butyllithium (nBuLi) is added dropwise, under inert gas and at -78° C., to 47.08 g of the product obtained in Stage A in 375 ml of tetrahydrofuran (THF), agitation is carried out for 1 hour, then 36.5 ml of triethylborate is added. Agitation is carried out for 14 hours, while leaving the temperature to rise to 20° C., and the reaction medium is hydrolyzed using a solution of ice-cooled water containing 45 ml of concentrated sulphuric acid, for 1 hour at 20° C. The aqueous phase is extracted with ethyl acetate, the organic phases are washed with 2N soda and the aqueous phase is acidified to pH=1 using a 1N solution of hydrochloric acid in order to precipitate the boronic acid. After filtration and drying the precipitate 28.54 g of expected product is obtained. Rf: 0.16 cyclohexane/ethyl acetate 7/3) I.R. spectrum: (Nujol)

Workup

  1. waitAgitation is carried out for 14 hours
  2. customwhile leaving the temperature
  3. customto rise to 20° C.
  4. waitfor 1 hour at 20° C
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. washthe organic phases are washed with 2N soda
  7. customto precipitate the boronic acid
  8. filtrationAfter filtration
  9. dry with materialdrying the precipitate 28.54 g of expected product
  10. customis obtained

Sources & evidence

ORD record
ord-d92d0684ffdb4cdd84ca7bc4be31060a
Source dataset
uspto-grants-2000_11
Patent number
US06147119

Reaction notes

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