Carbon tetrabromide → 5-Chloro-2-[3-(2,2-dibromovinyl)phenoxy]-pyrimidine

HRID 2295951Notes

Reaction equation

HRID 2295951 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:25][C:26]1[CH:27]=[N:28][C:29]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH:39]=O)[CH:34]=2)=[N:30][CH:31]=1>[Cl-]>[Cl:25][C:26]1[CH:31]=[N:30][C:29]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH:39]=[C:1]([Br:5])[Br:2])[CH:34]=2)=[N:28][CH:27]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 133365795-Chloro-2-(3-formylphenoxy)-pyrimidine

Product 1

HCID 133366365-Chloro-2-[3-(2,2-dibromovinyl)phenoxy]-pyrimidineYield 100.2%

Reagents, catalysts & solvents 1

HCID 312ChlorideSolvent

Procedure

Carbon tetrabromide (3.32 g) was added with stirring to a solution of triphenylphosphine (5.24 g) in methylne chloride (20 ml) at 20° C. 5-Chloro-2-(3-formylphenoxy)-pyrimidine (1.8 g) was added immediately to the warm orange solution causing the colour to fade rapidly. After 2 hours at 20° C. the reaction mixture was washed with water and then the organic layer was dried and concentrated to a thick syrup. Extraction of this syrup with n-hexane (4×50 ml), followed by evaporation of the n-hexane gave a colourless oil (3 g). The oil was chromatographed on a column of silica gel (50 g) and elution with chloroform gave the title compound, in the first fractions, as a colourless crystalline solid (1.95 g), m.p. 68° C.

Workup

  1. washAfter 2 hours at 20° C. the reaction mixture was washed with water
  2. customthe organic layer was dried
  3. concentrationconcentrated to a thick syrup
  4. extractionExtraction of this syrup with n-hexane (4×50 ml)
  5. customfollowed by evaporation of the n-hexane

Sources & evidence

ORD record
ord-33f914cf590045799a141f733e73b8f1
Source dataset
uspto-grants-1984_01
Patent number
US04427437

Reaction notes

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