9-Borabicyclo(3.3.1)nonane → 2-(4-Bromo-2-ethoxyphenyl)ethan-1-ol

HRID 735665Notes

Reaction equation

HRID 735665 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[C:4](C)[CH:3]=1.BrC1C=CC(C=C)=[C:15]([O:21]CC)[CH:14]=1.B1C2CCCC1CCC2>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[C:4]([O:21][CH2:15][CH3:14])[CH:3]=1

Participants

4

Reactant 3

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 578428364-Bromo-2-ethoxy-1-vinylbenzeneHCID 578428522-(4-Bromo-2-methylphenyl)ethanol2×

Product 1

HCID 578428372-(4-Bromo-2-ethoxyphenyl)ethan-1-olYield 82%

Procedure

Using a procedure analogous to that used to prepare 30B, 62D (700 mg, 3.3 mmol) was heated in a pressure vessel with 9-BBN at 100° C. for 10 h and worked up as in 30B to yield 62E (620 mg, 82%) as solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.41 (t, J=6.95 Hz, 3 H) 2.85 (t, J=6.32 Hz, 2 H) 3.81 (t, J=6.32 Hz, 2 H) 4.02 (q, J=7.07 Hz, 2 H) 6.96 (s, 1 H) 6.99-7.03 (m, 2 H).

Sources & evidence

ORD record
ord-830ba65fbef648d6b0ceb586f8440a6d
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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