Boron tribromide → HCID 22054946, compound

HRID 1829809Notes

Reaction equation

HRID 1829809 reaction equation
[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=2)[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22054975HCID 22054975, compound

Product 1

HCID 22054946HCID 22054946, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 2-benzyl-4-(3-methoxyphenyl)thiazole (1.0 g, 3.55 mmol) in CH2Cl2 (20 ml) was added a solution of 1.0 M BBr3 in CH2Cl2 (4.26 ml) at −78° C. The resulting mixture was stirred at −78° C. for 30 min and then allowed to warm up to room temperature. The mixture was quenched with water and extracted with ether. The organic layer was washed with brine, dried (magnesium sulfate) and evaporated in vacuo. The residue was triturated with chloroform and dried under reduced pressure to give 3-(2-benzylthiazol-4-yl)phenol (760 mg, 80%).

Workup

  1. temperatureto warm up to room temperature
  2. customThe mixture was quenched with water
  3. extractionextracted with ether
  4. washThe organic layer was washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated in vacuo
  7. customThe residue was triturated with chloroform
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-6ce5f3a04c494a1d8dc56bb0891769ba
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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