Pentane → 2-Heptyl-phenylboronic acid

HRID 2085597Notes

Reaction equation

HRID 2085597 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C([Li])(C)(C)C.CCCCC.[B:25](OC)([O:28]C)[O:26]C>O1CCCC1>[CH2:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[B:25]([OH:28])[OH:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 8003PentaneHCID 8470Trimethyl borateHCID 227313181-Bromo-2-heptyl-benzene2×HCID 178418306HCID 178418306, compound

Product 1

HCID 227313512-Heptyl-phenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure A and using 1-bromo-2-heptyl-benzene (Intermediate 67, 0.4 g, 1.56 mmol), 4 mL of anhydrous tetrahydrofuran, 1.7M solution of t-butyllithium in n-pentane (1.84 mL, 3.1 mmol) and trimethyl borate (0.45 mL, 3.1 mmol), the title compound was obtained (0.27 g, 50%).

Sources & evidence

ORD record
ord-26709f5f3ae0464cba4168e307ab99a6
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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