1-Chloro-4-(chloromethyl)benzene → 3-(5-Bromo-3-pyridyl)-4-(4-chlorophenyl)-2-butanol

HRID 133461Notes

Reaction equation

HRID 133461 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.BrC1C=C(CC(=O)C)C=CC=1.[Br:21][C:22]1[CH:23]=[C:24]([CH2:28][C:29](=[O:31])[CH3:30])[CH:25]=[N:26][CH:27]=1>>[Br:21][C:22]1[CH:23]=[C:24]([CH:28]([CH2:6][C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:29]([OH:31])[CH3:30])[CH:25]=[N:26][CH:27]=1

Participants

4

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 27340931-(3-Bromophenyl)propan-2-oneHCID 177501471-(5-Bromopyridin-3-yl)propan-2-one

Product 1

HCID 222704453-(5-Bromo-3-pyridyl)-4-(4-chlorophenyl)-2-butanol

Procedure

The title compound was prepared following the procedures described in Reference Example 40, Step B-C, substituting 2-bromomethyl-5-chloropyridine with 4-chlorobenzyl chloride and 3-bromophenylacetone with 5-bromo-3-pyridylacetone (Step A). 1H NMR (500 MHz, CD3OD): δ 8.43 (d, 1H), 8.24 (d, 1H), 7.98 (dd, 1H), 7.17 (d, 2H), 7.07 (d, 2H), 4.04 (m, 1H), 3.16 (dd, 1H), 3.0-2.9 (m, 2H), 1.04 (d, 3H).

Sources & evidence

ORD record
ord-ef763848021b4c3bade3a5ff56003b45
Source dataset
uspto-grants-2008_06
Patent number
US07390835B2

Reaction notes

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