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

HRID 735657Notes

Reaction equation

HRID 735657 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([Cl:21])C=1.B1C2CCCC1CCC2>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[C:4]([Cl:21])[CH:3]=1

Participants

4

Reactant 3

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 578427134-Bromo-2-chloro-1-ethenylbenzeneHCID 578428522-(4-Bromo-2-methylphenyl)ethanol2×

Product 1

HCID 578428022-(4-Bromo-2-chlorophenyl)ethan-1-olYield 54%

Procedure

Using a procedure analogous to that used to prepare 30B, 61A (5 g, 23 mmol) was heated in a pressure vessel with 9-BBN at 100° C. for 10 h and worked up as in 30B to yield 61B (2.9 g, 54%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.95 (t, J=6.59 Hz, 2 H) 3.85 (t, J=6.59 Hz, 2 H) 7.14 (d, J=7.91 Hz, 1 H) 7.33 (dd, J=8.13, 1.98 Hz, 1 H) 7.52 (d, J=2.20 Hz, 1 H).

Sources & evidence

ORD record
ord-5934a5e8f54d4467b71a53eb70fc897d
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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