Hydrochloric Acid → 3-Benzyloxy-phenylboronic acid

HRID 2399191Notes

Reaction equation

HRID 2399191 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[B:17](OC)([O:20]C)[O:18]C.Cl>O1CCCC1.O.II>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([B:17]([OH:20])[OH:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 27566381-(Benzyloxy)-3-bromobenzeneHCID 5462224Magnesium

Product 1

HCID 27343133-Benzyloxy-phenylboronic acidYield 62.5%

Reagents, catalysts & solvents 3

HCID 807IodineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

62 g (0.236 mol) of 3-benzyloxybromobenzene, 6.64 g (0.277 mol) of magnesium and 0.3 g of iodine are reacted in 800 ml of tetrahydrofuran at 60° C. for 2 hours to give the solution of the corresponding Grignard compound, which is subsequently added dropwise to a solution, cooled to 0° C. of 28.77 g (0.277 mol) of trimethyl borate in 300 ml of tetrahydrofuran. The mixture is stirred at 0° C. for 1 hour, 74 ml of 37% strength hydrochloric acid in 300 ml of water are added, and the reaction mixture is subsequently partitioned between water and ether. The organic phase is washed twice with water, dried over sodium sulfate, evaporated and recrystallized from hexane, giving 33.65 g of 3-benzyloxybenzeneboronic acid. ##STR13##

Workup

  1. customto give the solution of the corresponding Grignard compound, which
  2. additionis subsequently added dropwise to a solution
  3. customthe reaction mixture is subsequently partitioned between water and ether
  4. washThe organic phase is washed twice with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customrecrystallized from hexane

Sources & evidence

ORD record
ord-74ddc87aa2504f00be47ec1fc3f5923b
Source dataset
uspto-grants-1995_09
Patent number
US05447656

Reaction notes

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