Toluene → 5-Bromo-2-(3-(chloromethyl)phenoxy)pyrimidine

HRID 1666377Notes

Reaction equation

HRID 1666377 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH2:15]O)[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.S(Cl)([Cl:19])=O.C1(C)C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][Cl:19])[CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 63869081(3-(5-Bromopyrimidin-2-yloxy)phenyl)methanol

Product 1

HCID 668767225-Bromo-2-(3-(chloromethyl)phenoxy)pyrimidineYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-(5-Bromopyrimidin-2-yloxy)phenyl)methanol (0.790 g, 2.81 mmol) in dichloromethane (9 mL) was cooled to 0° C. and treated dropwise with thionyl chloride (0.215 mL, 2.95 mmol). The reaction mixture was allowed to warm to ambient temperature and stirred for 1 h. Toluene (5 mL) was added and the mixture was concentrated to give the title compound (0.815 g, 97% yield) as a semi-solid. MS (APCI) M+1=299.0.

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-b27e70a88f364a468843a5c32c34da9e
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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