Tetrahydrofuran → Formylphenylboronic acid

HRID 2308031Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:5](C=O)=[CH:4][CH:3]=1.[Mg].[B:11]([O:22][CH2:23]CCC)([O:17]CCCC)OCCCC.[O:27]1CCCC1>>[CH:23]([O:22][B:11]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:8][CH:9]=1)[OH:17])=[O:27]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 12712Tributyl borate

HCID 707414-Bromobenzaldehyde

HCID 5462224Magnesium

Product 1

HCID 66687538Formylphenylboronic acidYield 70%

Procedure

Nöth et al. (Chem. Ber. 1990, 1841-1843) convert p-bromobenzaldehyde into the diethyl acetal, convert this into the corresponding Grignard reagent by means of magnesium turnings in tetrahydrofuran (THF) and, after reaction with tri-n-butyl borate, obtain formylphenylboronic acid in a yield of 70%. A disadvantage of this synthesis is the high price of bromobenzaldehyde compared to chlorobenzaldehyde, the need for ultrasonic activation in the preparation of the Grignard reagent and the use of the expensive tributyl borate; in addition, complicated purification procedures have to be employed (e.g. via the hydrolysis product 1-butanol).

Sources & evidence

ORD record: ord-502cea095e6a4f8cb24d6b805e00cd30
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06833470B2

Reaction notes

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