Trimethyl borate → (4-(Decyloxy)phenyl)boronic acid

HRID 1459097Notes

Reaction equation

HRID 1459097 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])=[CH:4][CH:3]=1.C([Li])CCC.[B:24](OC)([O:27]C)[O:25]C.C(OC1C=CC(B(O)O)=CC=1)CCCCCCC>C1COCC1>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([B:24]([OH:27])[OH:25])=[CH:3][CH:4]=1)[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 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)HCID 105671431-Bromo-4-decyloxybenzeneHCID 178418339Butyllithium

Product 1

HCID 10612601(4-(Decyloxy)phenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Quantities: compound 28 (9.39 g, 0.03 mol) in anhydrous THF (100 ml), n-butyllithium (12.1 ml, 2.5M in hexane, 0.03 mol), trimethyl borate (6.24 g, 0.066 mol) in anhydrous THF (20 ml). The experimental procedure was as described for the preparation of compound 33.

Sources & evidence

ORD record
ord-c48fea2202c5492fa1ceb2fd5c643e79
Source dataset
uspto-grants-1998_12
Patent number
US05853613

Reaction notes

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