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.
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Applications
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.
Solubility
Sparingly soluble in water.
Notes
Moisture Sensitive. Store at 4°C. Do not store together with acids. Store away from water and strong bases. Incompatible with acids, bases, moisture, heat and oxidizing agents.
RUO – Research Use Only
General References:
- 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).