1,1,1-Trimethoxy-2-chloroethane → 5-Bromo-2-(chloromethyl)-1,3-benzoxazole

HRID 1916760Notes

Reaction equation

HRID 1916760 reaction equation
[Cl:1][CH2:2][C:3](OC)(OC)[O:4][CH3:5].[NH2:10][C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13]C=1O>C(O)C>[Br:17][C:15]1[CH:14]=[CH:13][C:5]2[O:4][C:3]([CH2:2][Cl:1])=[N:10][C:11]=2[CH:16]=1

Participants

4

Reactant 2

HCID 1447021,1,1-Trimethoxy-2-chloroethane2×HCID 3518402-Amino-4-Bromophenol

Product 1

HCID 142042085-Bromo-2-(chloromethyl)-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.79 mL (13.3 mmol) 2-chloro-1,1,1-trimethoxy-ethane are added dropwise at RT to a solution of 2.5 g (13.29 mmol) 2-amino-4-bromophenol in 20 mL ethanol and stirred for 48 h. Then 0.4 mL 2-chloro-1,1,1-trimethoxy-ethane are added and stirred for 20 h. The reaction mixture is evaporated down. The purification is carried out by column chromatography on silica gel (DCM/ethanol 80:1).

Workup

  1. stirringstirred for 20 h
  2. customThe reaction mixture is evaporated down
  3. customThe purification

Sources & evidence

ORD record
ord-b624282bf66640a0a9b1fad8ffced8b0
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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