9-Borabicyclo(3.3.1)nonane → 2-(4-Bromo-2,6-diethylphenyl)ethanol

HRID 735605Notes

Reaction equation

HRID 735605 reaction equation
BrC1C=CC(CC[OH:10])=C(C)C=1.[Br:12][C:13]1[CH:14]=[C:15]([CH2:23][CH3:24])[C:16]([CH:21]=[CH2:22])=[C:17]([CH2:19][CH3:20])[CH:18]=1.B1C2CCCC1CCC2>>[Br:12][C:13]1[CH:18]=[C:17]([CH2:19][CH3:20])[C:16]([CH2:21][CH2:22][OH:10])=[C:15]([CH2:23][CH3:24])[CH:14]=1

Participants

4

Reactant 3

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 578428522-(4-Bromo-2-methylphenyl)ethanolHCID 578429095-Bromo-1,3-diethyl-2-vinylbenzene

Product 1

HCID 578429172-(4-Bromo-2,6-diethylphenyl)ethanolYield 58%

Procedure

Using a procedure analogous to that used to prepare 30B, 37B (1.2 g, 5 mmol) was heated in a pressure vessel with 9-BBN at 115° C. for 1 h to yield 37C (735 mg, 58%) as an orange oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.21 (t, J=7.58 Hz, 6 H) 2.66 (q, J=7.49 Hz, 4 H) 2.92 (t, J=7.58 Hz, 2 H) 3.66-3.77 (t, J=7.57 Hz, 2 H) 7.17 (s, 2 H).

Sources & evidence

ORD record
ord-8b75bed6e566417687c705a7899609c0
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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