4-Bromoanisole → (4-Methoxyphenyl)boronic acid

HRID 1964797Notes

Reaction equation

HRID 1964797 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Li]CCCC.C([O:19][B:20]([O-])[O-:21])CCC>C1COCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([B:20]([OH:21])[OH:19])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 77304-BromoanisoleHCID 86592051n-ButylborateHCID 178418339Butyllithium

Product 1

HCID 201262(4-Methoxyphenyl)boronic acidYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromoanisole (100 g, 0.53 mol) in dry THF (1 L), BuLi (494 ml-, 0.64 mol) was added slowly at −78° C. and stirred for 2 h. To this was added n-butylborate (147 g, 0.64 mol) slowly over 30 min and stirred at RT for 12 h. After completion, the reaction mixture was quenched with water (400 ml), acidified with 1.5N HCl and filtered off the solid precipitate. The solid was washed with water and dried to give 4-methoxyphenylboronic acid (75 g, 92%).

Workup

  1. stirringstirred at RT for 12 h
  2. customAfter completion, the reaction mixture was quenched with water (400 ml)
  3. filtrationfiltered off the solid precipitate
  4. washThe solid was washed with water
  5. customdried

Sources & evidence

ORD record
ord-de3519c4b26d4939ae30e3f4b546a8b8
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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