Sulfuric Acid → 4-tert-Butylphenylboronic acid

HRID 2118148Notes

Reaction equation

HRID 2118148 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([Mg]Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(Br)=CC=1)(C)(C)C.[Mg].[B:25](OCCCC)([O:31]CCCC)[O:26]CCCC.S(=O)(=O)(O)O>C(OCC)C.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([B:25]([OH:31])[OH:26])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 12712Tributyl borateHCID 775951-Bromo-4-tert-butylbenzeneHCID 5462224MagnesiumHCID 178440986HCID 178440986, compound

Product 1

HCID 27343204-tert-Butylphenylboronic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of para-tert-butylphenyl magnesium bromide prepared from 52 ml of para-tert-butylphenyl bromide and 8.0 g of the magnesium turnings in 250 ml of diethyl ether was added to 81 ml of tri-n-butyl borate in 250 ml of diethyl ether at −80° C. with stirring under argon. The reaction mixture was allowed to warm to ambient temperature, and was poured into 150 ml of 10% sulfuric acid in water. The organic phase was extracted twice by 100 ml of diethyl ether. The solvent and n-butanol were removed under vacuum. The viscous residue was recrystallized from boiling water. Yield of 4-tert-butylphenyl boronic acid was 10% as white crystals with mp. 202-203° C.

Workup

  1. extractionThe organic phase was extracted twice by 100 ml of diethyl ether
  2. customThe solvent and n-butanol were removed under vacuum
  3. customThe viscous residue was recrystallized

Sources & evidence

ORD record
ord-69003c5ef3bf48b6b2d10a4591723fa1
Source dataset
uspto-grants-2008_10
Patent number
US07442819B2

Reaction notes

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