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

HRID 3925

Reaction equation

HRID 3925 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Cl:10][CH2:11][C:12](OCC)(OCC)OCC.O>C(O)C>[Cl:10][CH2:11][C:12]1[O:9][C:3]2[CH:4]=[CH:5][C:6]([Br:8])=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3059222-Chloro-1,1,1-triethoxyethaneHCID 3518402-Amino-4-Bromophenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-4-bromophenol (1.6 g) prepared according to U.S. Pat. No. 4,157,444 was dissolved in ethanol (5 ml) and 2-chloro-1,1,1-triethoxyethane (1.9 g) was added. The resulting solution was warmed on a steambath for 1.5 hour. After cooling the reaction mixture to room temperature, cold water (5 ml) was added. The precipitated solid was collected and air-dried to obtain the product (1.12 g; m.p. 63°-65° C.

Workup

  1. temperatureThe resulting solution was warmed on a steambath for 1.5 hour
  2. customThe precipitated solid was collected
  3. customair-dried
  4. customto obtain the product (1.12 g

Sources & evidence

ORD record
ord-8ec63ae82f0647afb2a58c8cce47600d
Source dataset
uspto-grants-1988_02
Patent number
US04723010

Linked notes

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