Hydrochloric Acid → 5-Ethoxymethoxy-2-methylphenylboronic acid

HRID 584286Notes

Reaction equation

HRID 584286 reaction equation
[Mg].Br[C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH2:12][CH3:13])[CH:6]=[CH:5][C:4]=1[CH3:14].[B:15](OC(C)C)([O:20]C(C)C)[O:16]C(C)C.Cl>O1CCCC1>[CH2:12]([O:11][CH2:10][O:9][C:7]1[CH:6]=[CH:5][C:4]([CH3:14])=[C:3]([B:15]([OH:20])[OH:16])[CH:8]=1)[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 5462224MagnesiumHCID 223455862-Bromo-4-ethoxymethoxy-1-methylbenzene

Product 1

HCID 223456045-Ethoxymethoxy-2-methylphenylboronic acidYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.4 g (59 mmol) of magnesium turnings are placed in tetrahydrofuran in a round-bottomed flask and under a stream of nitrogen. 13.2 g (54 mmol) of 2-bromo-4-ethoxymethoxy-1-methylbenzene diluted in a small amount of THF are added slowly. The medium is refluxed for 20 minutes. It is then added via a cannula to 15 ml (65 mmol) of triisopropyl borate. The mixture sets to a solid and is then poured into 1N hydrochloric acid solution and extracted with ether. The organic phase is dried over magnesium sulfate, filtered and then evaporated. 9.8 g (87%) of the expected product are obtained in the form of a brown oil.

Workup

  1. additionare added slowly
  2. temperatureThe medium is refluxed for 20 minutes
  3. extractionextracted with ether
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-229c39ba6be9404ebf6c654717af294a
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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