9-Borabicyclo(3.3.1)nonane → 2-(4-Bromo-2-ethylphenyl)ethanol

HRID 735598Notes

Reaction equation

HRID 735598 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[C:4]([CH3:11])[CH:3]=1.Br[C:13]1C=CC(C=C)=C(CC)C=1.B1C2CCCC1CCC2>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[C:4]([CH2:11][CH3:13])[CH:3]=1

Participants

4

Reactant 3

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 578426424-Bromo-2-ethyl-1-vinylbenzeneHCID 578428522-(4-Bromo-2-methylphenyl)ethanol

Product 1

HCID 578427842-(4-Bromo-2-ethylphenyl)ethanolYield 81%

Procedure

Using a procedure analogous to that used to prepare 30B, 36A (1.98 g, 5.1 mmol) was heated in a pressure vessel with 9-BBN at 100° C. for 15 h to yield 36B (0.95 g, 81%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.23 (t, J=7.58 Hz, 3 H) 2.66 (q, J=7.58 Hz, 2 H) 2.87 (t, J=6.82 Hz, 2 H) 3.83 (t, J=6.82 Hz, 2 H) 7.06 (d, J=8.08 Hz, 1 H) 7.25-7.31 (m, 1 H) 7.32-7.37 (m, 1 H).

Sources & evidence

ORD record
ord-b181d80d577c42a989d4b00064e7f529
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…