Trimethyl borate → 3-Fluoro-4-decyloxyphenylboronic acid

HRID 1459093Notes

Reaction equation

HRID 1459093 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:4]([F:19])[CH:3]=1.C([Li])CCC.[B:25](OC)([O:28]C)[O:26]C.FC1C(F)=CC=CC=1B(O)O>C1COCC1>[F:19][C:4]1[CH:3]=[C:2]([B:25]([OH:28])[OH:26])[CH:7]=[CH:6][C:5]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 8470Trimethyl borateHCID 2734333(2,3-Difluorophenyl)boronic acidHCID 146925094-Decyloxy-3-fluorophenyl bromideHCID 178418339Butyllithium

Product 1

HCID 118085913-Fluoro-4-decyloxyphenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Quantities: compound 12 (9.84 g, 0.03 mol) in anhydrous THF (120 ml), n-butyllithium (12.5 ml, 2.5M in hexane, 0.031 mol), trimethyl borate (6.24 g, 0.06 mol) in anhydrous THF (50 ml). The experimental procedure was as described for the preparation of compound 2.

Sources & evidence

ORD record
ord-3175eb18c3744305be2f0fefe66781f1
Source dataset
uspto-grants-1998_12
Patent number
US05853613

Reaction notes

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