4-Bromoanisole → 4-Methoxyphenyl boric acid

HRID 477046Notes

Reaction equation

HRID 477046 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C(=O)=O.CC(C)=O.CCCCCC.[B:23]([O:32]C(C)C)([O:28]C(C)C)[O:24]C(C)C>O1CCCC1.CCOCC>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([O:24][B:23]([OH:32])[OH:28])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 77304-BromoanisoleHCID 8058HexaneHCID 21531Triisopropyl borateHCID 18522661Acetone cardice

Product 1

HCID 147699944-Methoxyphenyl boric acidYield 67.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

13.09 g of 4-Bromoanisole was dissolved in 50 ml of tetrahydrofuran, and the solution was cooled to -78° C. with a dry ice-acetone freezing mixture, and 48 ml of m-butyllithium (as a 1.6 M hexane solution). The mixture was stirred for 10 minutes. A tetrahydrofuran solution of 32 ml of triisopropyl borate was added dropwise under cooling over the course of 30 minutes. The temperature of the solution was returned to room temperature, and it was stirred for 10 minutes. Ether was added to the reaction solution, and it was washed with a 10% aqueous solution of hydrochloric acid and water in this order. The solvent was evaporated, and the resulting solid was recrystallized from ether-hexane to give 7.18 g (yield 67.5%) of (4-methoxyphenyl)boric acid as colorless needles having a melting point of 157° to 159° C.

Workup

  1. temperatureunder cooling over the course of 30 minutes
  2. customwas returned to room temperature
  3. stirringit was stirred for 10 minutes
  4. washwas washed with a 10% aqueous solution of hydrochloric acid and water in this order
  5. customThe solvent was evaporated
  6. customthe resulting solid was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-583839d466bb482bac83fdb8484f5bc5
Source dataset
uspto-grants-1989_12
Patent number
US04886822

Reaction notes

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