Triisopropyl borate → 3-(Benzyloxy)-4-(trifluoromethyl)phenylboronic acid

HRID 1639919Notes

Reaction equation

HRID 1639919 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[C:16]([F:19])([F:18])[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[B:25](OC(C)C)([O:30]C(C)C)[O:26]C(C)C>>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([B:25]([OH:30])[OH:26])[CH:12]=[CH:11][C:10]=1[C:16]([F:19])([F:18])[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 21531Triisopropyl borateHCID 667210242-(Benzyloxy)-4-iodo-1-(trifluoromethyl)benzeneHCID 178418918HCID 178418918, compound

Product 1

HCID 567766183-(Benzyloxy)-4-(trifluoromethyl)phenylboronic acidYield 79%

Procedure

According to the method described in example 4.2, starting from 8 g (21.2 mmol) of 2-(benzyloxy)-4-iodo-1-(trifluoromethyl)benzene, 11.1 mL (22.2 mmol) of iPrMgCl and 5 mL (21.6 mmol) of triisopropyl borate, we obtain 4.95 g of [3-(benzyloxy)-4-(trifluoromethyl)phenyl]boronic acid in the form of oil.

Sources & evidence

ORD record
ord-b2d6d44e681e418bba527224cd2d6e39
Source dataset
uspto-grants-2012_02
Patent number
US08110579B2

Reaction notes

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