Trimethyl borate → [4-(Dodecyloxy)phenyl]boronic acid

HRID 1459099Notes

Reaction equation

HRID 1459099 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][CH2:18][CH2:19][CH3:20])=[CH:4][CH:3]=1.C([Li])CCC.[B:26](OC)([O:29]C)[O:27]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:26]([OH:29])[OH:27])=[CH:3][CH:4]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 8470Trimethyl borateHCID 287462HCID 287462, compoundHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)HCID 178418339Butyllithium

Product 1

HCID 15790446[4-(Dodecyloxy)phenyl]boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Quantities: compound 30 (15.00 g, 0.047 mol) in anhydrous THF (150 ml), n-butyllithium (20 ml, 2.5M in hexane, 0.050 mol), trimethyl borate (9.79 g, 0.094 mol) in anhydrous THF (50 ml). The experimental procedure was as described for the preparation of compound 33.

Sources & evidence

ORD record
ord-a5e5c5b422d04fe1a380128b73001908
Source dataset
uspto-grants-1998_12
Patent number
US05853613

Reaction notes

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