Bis(2-bromoethyl) ether → HCID 20255643, compound

HRID 637693Notes

Reaction equation

HRID 637693 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]2[C:6]([CH3:9])=[CH:7][O:8][C:4]=2[CH:3]=1.[CH2:13]([O:16][CH2:17][CH2:18]Br)[CH2:14]Br.C(N(C(C)C)C(C)C)C>C(O)C>[CH3:9][C:6]1[C:5]2[CH:10]=[C:11]([CH3:12])[C:2]([N:1]3[CH2:18][CH2:17][O:16][CH2:13][CH2:14]3)=[CH:3][C:4]=2[O:8][CH:7]=1

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 20255642HCID 20255642, compound

Product 1

HCID 20255643HCID 20255643, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 22.8 g (0.141 mole) of 6-amino-3,5-dimethylbenzofuran, 65.8 g (0.283 mole) of 2,2'-dibromodiethyl ether, 36.1 g (0.279 mole) of N-ethyldiisopropylamine and 210 ml of ethanol is boiled under reflux for 16 hours. The residue obtained after removal of the ethanol in vacuo is taken up in methylene chloride and washed twice with dilute sodium bicarbonate solution. The organic phase is dried, concentrated by evaporation and the crude product is chromatographed over silica gel with petroleum ether/ether. The excess 2,2'-dibromodiethyl ether is removed in a water-jet vacuum over a Vigreux column and the residue is purified by means of solid distillation (110°-115°/4.10-2 torr). 3,5-dimethyl-6-morpholinobenzofuran is obtained having a melting point of 69°-70°.

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe residue obtained
  3. customafter removal of the ethanol in vacuo
  4. washwashed twice with dilute sodium bicarbonate solution
  5. customThe organic phase is dried
  6. concentrationconcentrated by evaporation
  7. customthe crude product is chromatographed over silica gel with petroleum ether/ether
  8. customThe excess 2,2'-dibromodiethyl ether is removed in a water-jet vacuum over a Vigreux column
  9. distillationthe residue is purified by means of solid distillation (110°-115°/4.10-2 torr)

Sources & evidence

ORD record
ord-485abc0651964e75879e61813edb7794
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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