Reaction #302886

Reaction equation

sodium methoxide

o-bromobenzyl bromide

toluene

water

→

1-methoxymethyl-2-bromobenzene

Solvents

methanol

methanol

Conditions

Workup

1. 1
   Otherlayers were separated
2. 2
   Otheran organic layer was recovered
3. 3
   ExtractionAn aqueous layer was extracted with 211 g of toluene three times
4. 4
   workup.ADDITIONthe recovered organic layer and 211 g of water were added
5. 5
   Washthis was washed
6. 6
   Concentrationconcentrated

Procedure

A temperature of 59.8 g of a 28% solution of sodium methoxide in methanol was raised to 60° C., a mixture solution of 70.4 g of o-bromobenzyl bromide and 70.4 g of methanol was added dropwise, and this was retained at 60° C. for 2 hours. After the mixture was cooled to room temperature, 211 g of toluene and 211 g of water were added thereto, the mixture was stirred, and layers were separated, and an organic layer was recovered. An aqueous layer was extracted with 211 g of toluene three times, the recovered organic layer and 211 g of water were added, and this was washed, and concentrated to obtain 55.3 g of 1-methoxymethyl-2-bromobenzene.

Source