Pyridine → 4-Methoxybenzyl 2-bromoacetate

HRID 1981180Notes

Reaction equation

HRID 1981180 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[Cl-].[Cl-].[Ca+2].N1C=CC=CC=1.[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][OH:22])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Br:1][CH2:2][C:3]([O:22][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)=[O:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 77384-Methoxybenzyl alcoholHCID 61147Bromoacetyl bromideHCID 5284359Calcium Chloride

Product 1

HCID 132332344-Methoxybenzyl 2-bromoacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

20.2 g (0.1 mol) of bromoacetyl bromide are dissolved in 100 ml of toluene, this solution is cooled to -10° C. (CaCl2 tube) and 8.7 g (0.11 mol) of pyridine are added dropwise at -10° C. Thereafter, 13.8 g (0.1 mol) of 4-methoxybenzyl alcohol, dissolved in 20 ml of toluene are added dropwise to this mixture in the course of 20 minutes at -10° C., and the mixture is allowed to react for 1 hour at this temperature.

Workup

  1. additionare added dropwise at -10° C
  2. additionare added dropwise to this mixture in the course of 20 minutes at -10° C.
  3. customto react for 1 hour at this temperature

Sources & evidence

ORD record
ord-5daf8af4fbfd450892b0c994d83359d4
Source dataset
uspto-grants-1985_04
Patent number
US04513004

Reaction notes

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