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Bromomethyl methyl ether is used as reagent for protection of OH groups as their methoxymethyl (MOM) ethers. It is used in enantiocontrolled synthesis of intermediate containing carbons 18 to 35 of the macrocyclic immunosuppressant FK-506. It was used in the synthesis of 1-methoxymethyl-4-tritylthio-2-azetidinone.
Takeshi Oriyama; Mikio Kimura; Gen Koga. A One-Step Conversion of p-Methoxybenzyl Ethers into Methoxymethyl Ethers by the Action of Dimethoxymethane in the Presence of Tin(II) Bromide and Bromomethyl Methyl Ether.Bulletin of the Chemical Society of Japan.1994, 67 (3), 885-887.
Reagent for protection of OH groups as their methoxymethyl (MOM) ethers. The group can be introduced in the presence of a base such as N-ethyldiisopropylamine: Tetrahedron Lett., 26, 6461 (1986); 30, 1971 (1989). Aryl acetates are converted directly into aryl methoxymethyl ethers in the presence of NaOMe in DMF: Synth. Commun., 29, 2217 (1999).
A method for the ɑ-methylenation of lactones involves alkylation of the ɑ-lithio derivative, followed by elimination of methanol: J. Am. Chem. Soc., 102, 3964 (1980).
For a review of the use of ɑ-monohalo ethers in synthesis, see: Synthesis, 1 (1995).
Hazard Statements: H226-H302-H312-H332-H315-H319-H351-H335
Flammable liquid and vapour. Harmful if swallowed. Harmful in contact with skin. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. Suspected of causing cancer. May cause respiratory irritation.
Precautionary Statements: P210-P201-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Obtain special instructions before use. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.