Chloromethyl Methyl Ether → HCID 12087966, compound

N,N-Diisopropylethylamine (8.3 mL, 47.4 mmol) (Aldrich) was added to a suspension of 5-iodo-2-methyl-phenol (10.1 g, 43.1 mmol) (from Example 17 supra) in dichloromethane (40 mL) with cooling in an ice-water bath. Chloromethyl-methyl ether (6.5 mL, 86.1 mmol) (Aldrich) was added dropwise and the mixture stirred at room temperature for 5 hours. The mixture was then diluted with ether (200 mL) and washed with water (200 mL), followed by 0.1 N HCl (2×200 mL) and brine (200 mL). Aqueous layers were back washed with ether (200 mL). Organic solutions were combined, dried (MgSO4), filtered and concentrated. Residue was filtered through silica gel (Biotage 40 L) eluting with dichloromethane-hexenaes (1:4 V/v). Fractions were combined and concentrated to give 4-iodo-2-methoxymethoxy-1-methyl-benzene as colorless oil. (Yield 9.05 g, 75.6%).

1. temperaturewith cooling in an ice-water bath
2. washwashed with water (200 mL)
3. washAqueous layers were back washed with ether (200 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. filtrationResidue was filtered through silica gel (Biotage 40 L)
8. washeluting with dichloromethane-hexenaes (1:4 V/v)
9. concentrationconcentrated

ORD record

ord-ccde8cd001784e27904b7e5943c03419

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932390B2