Bis(neopentyl glycolato)diboron → 5-(4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)pentanoic acid

HRID 735498Notes

Reaction equation

HRID 735498 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][O:6][B:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17](O)=O)=[CH:10][CH:9]=2)[O:4][CH2:3]1.BrC1C=CC(CCCC[C:32]([OH:34])=[O:33])=CC=1.CC1(C)COB(B2OCC(C)(C)CO2)OC1>>[CH3:1][C:2]1([CH3:20])[CH2:7][O:6][B:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:32]([OH:34])=[O:33])=[CH:10][CH:9]=2)[O:4][CH2:3]1

Participants

4

Reactant 3

HCID 2734316Bis(neopentyl glycolato)diboronHCID 108011195-(4-Bromophenyl)pentanoic acidHCID 578427774-[4-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-phenyl]-butyric acid

Product 1

HCID 578428175-(4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)pentanoic acidYield 71%

Procedure

Using a procedure analogous to that used to prepare 2A, 5-(4-bromophenyl)pentanoic acid (537 mg, 2.09 mmol) was reacted with 5,5,5′,5′-Tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to afford 5A (429 mg, 71%) as a white solid. 1H NMR (400 MHz, tetrahydrofuran-d8) δ 0.99 (s, 6H), 1.55-1.70 (m, 4H), 2.24 (t, J=7.5 Hz, 2H), 2.61 (t, J=7.0 Hz, 2H), 3.73 (s, 4H), 7.12 (d, J=7.9 Hz, 2H), 7.65 (d, J=7.9 Hz, 2H).

Sources & evidence

ORD record
ord-70b695ec9666465ca8135c57fc85cc46
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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