Chloromethyl Methyl Ether → 1-Bromo-4-methoxy-2-(methoxymethoxy)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].C([O-])([O-])=O.[K+].[K+].[CH3:17][O:18][CH2:19]Cl>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:17][O:18][CH3:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
Protected haloorganoboronic acid 14 was synthesized by a multi-step process. To a stirred mixture of 2-bromo-5-methoxyphenol (Albert, 2002) (2.19 g, 10.8 mmol) and K2CO3 (4.46 g, 32.3 mmol) in acetone (55 mL) was added chloromethyl methyl ether (1.63 mL, 21.5 mmol). The mixture was refluxed for 3 h and then allowed to cool to 23° C. The mixture was filtered and the filtrate was concentrated in vacuo. The crude product was then purified by flash chromatography (SiO2, hexanes:EtOAc 95:5) to provide 2-bromo-5-methoxy-1-methoxymethoxybenzene as a colorless liquid (2.43 g, 92%).
Workup
- temperatureThe mixture was refluxed for 3 h
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated in vacuo
- customThe crude product was then purified by flash chromatography (SiO2, hexanes:EtOAc 95:5)
Sources & evidence
- ORD record
- ord-1709fbfcc68f4ff5b4fb074f1946c529
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318983B2
Reaction notes
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