Acetic Acid → 2-Bromo-4-(2-nitroethenyl)phenol

HRID 1287650Notes

Reaction equation

HRID 1287650 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.C(N)CC.[N+:15]([CH3:18])([O-:17])=[O:16].C(O)(=O)C>C1C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[CH:18][N+:15]([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 7852PropylamineHCID 763083-Bromo-4-hydroxybenzaldehyde

Product 1

HCID 540856812-Bromo-4-(2-nitroethenyl)phenol

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

3-Bromo-4-hydroxybenzaldehyde (20.1 g.) and n-propylamine (7.6 g.) were refluxed in dry benzene (150 ml.) using Dean-Stark water separator for 3 hours. Benzene phase was concentrated to get the crude aldimine as an oily product. The aldimine (24.2 g), nitromethane (24 ml.) and glacial acetic acid (72 ml.) were refluxed for 45 minutes. The reaction mixture was diluted with cold water. The solid was filtered off and crystallised from aqueous ethanol to obtain the title product; m.p. 132°-34° C.

Workup

  1. concentrationBenzene phase was concentrated
  2. customto get the crude aldimine as an oily product
  3. filtrationThe solid was filtered off
  4. customcrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-e443beb3c7614783a17d7ec59e4d12ed
Source dataset
uspto-grants-1976_10
Patent number
US03985761

Reaction notes

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