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

HRID 735588Notes

Reaction equation

HRID 735588 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=C(C)C(C=C)=C(C)C=1.B1C2CCCC1CCC2>>[Br:1][C:2]1[CH:7]=[C:6]([CH3:13])[C:5]([CH2:8][CH2:9][OH:10])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 3

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 534183645-Bromo-1,3-dimethyl-2-vinylbenzeneHCID 578428522-(4-Bromo-2-methylphenyl)ethanol

Product 1

HCID 578427022-(4-Bromo-2,6-dimethylphenyl)ethanolYield 62%

Procedure

Using a procedure analogous to that used to prepare 30B, 32A was heated in a pressure vessel with 9-BBN at 100° C. for 10 h to yield 32B (6.7 g, 62%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.31 (s, 6 H) 2.89 (t, J=7.33 Hz, 2 H) 3.73 (t, J=7.33 Hz, 2 H) 7.16 (s, 2 H).

Sources & evidence

ORD record
ord-1e608d1e4f2a4a089867903bf278d7bc
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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