2-(5-Bromopyridin-2-yl)ethan-1-ol → 5-Bromo-2-(2-iodoethyl)pyridine

HRID 533530Notes

Reaction equation

HRID 533530 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9]O)=[N:6][CH:7]=1.BrC1C=CC(CC[I:20])=CN=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][I:20])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 534036882-(5-Bromopyridin-2-yl)ethan-1-ol2×HCID 866687632-Bromo-5-(2-iodoethyl)pyridine

Product 1

HCID 665779095-Bromo-2-(2-iodoethyl)pyridineYield 77%

Procedure

The title compound (3571 mg, 77%) was prepared from 2-(5-bromopyridin-2-yl)ethanol (Compound 6, Preparation 4) (3.0 g, 14.9 mmol) by a procedure analogous to that described for the preparation of 2-bromo-5-(2-iodoethyl)pyridine in Preparation 2, Step 1. MS (LCMS) m/z 312.0 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.24-3.36 (m, 2H) 3.41-3.56 (m, 2H) 7.06 (d, J=8.20 Hz, 1H) 7.74 (dd, J=8.20, 2.34 Hz, 1H) 8.60 (d, J=2.34 Hz, 1H).

Sources & evidence

ORD record
ord-22e68cb4d116409a98e2ba8c034a3545
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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