Boron tribromide → HCID 12800895, compound

HRID 1413045Notes

Reaction equation

HRID 1413045 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([S:8][C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 12800894HCID 12800894, compound

Product 1

HCID 12800895HCID 12800895, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

5-Chloro-2-(4-methoxyphenylthio)pyrimidine (7.5 g) was dissolved in methylene chloride (60 ml) and the solution was cooled to -78° C. Boron tribromide (18 g) was added dropwise to the stirred solution, the temperature of the solution being maintained at -65° to -75° C. On completion of the addition the reaction mixture was stirred for a further one hour at -78° C. and then the temperature of the reaction mixture was allowed to rise slowly to 20° C. The reaction was quenched with water (50 ml), the resultant suspension cooled and filtered to give 4-(5-chloro-2-pyrimidylthio)phenol (5 g) as an almost colourless solid.

Workup

  1. temperaturethe temperature of the solution being maintained at -65° to -75° C
  2. additionOn completion of the addition the reaction mixture
  3. customto rise slowly to 20° C
  4. customThe reaction was quenched with water (50 ml)
  5. temperaturethe resultant suspension cooled
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ce3f7630135f4f43b49059ddbac1c8e4
Source dataset
uspto-grants-1981_02
Patent number
US04248618

Reaction notes

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