Boron tribromide → HCID 57417096, compound

HRID 1430163Notes

Reaction equation

HRID 1430163 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=2)([CH3:14])[CH3:13])[CH:7]=1>C(Cl)Cl>[Br:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]([C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)([CH3:13])[CH3:14])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57417097HCID 57417097, compound

Product 1

HCID 57417096HCID 57417096, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

BBr3 (1 M in DCM, 23 mmol, 8 eq) is added dropwise to a cold (0° C.) solution of 4-bromo-2-[1-(4-methoxy-phenyl)-1-methyl-ethyl]-pyridine (Step 55.3) (0.878 g, 2.87 mmol) in DCM (42 mL), under an argon atmosphere. The reaction mixture is stirred for 1 h at 0° C., allowed to warm to rt, stirred for 18 h, cooled to 0° C. and quenched by addition of anhydrous MeOH. The mixture is concentrated, diluted with a 6M aqueous solution of HCl, stirred for 1 h, neutralized to pH 7 and extracted with DCM. The organic phase is dried (Na2SO4), filtered and concentrated. The residue is used without purification.

Workup

  1. temperatureto warm to rt
  2. stirringstirred for 18 h
  3. temperaturecooled to 0° C.
  4. customquenched by addition of anhydrous MeOH
  5. concentrationThe mixture is concentrated
  6. additiondiluted with a 6M aqueous solution of HCl
  7. stirringstirred for 1 h
  8. extractionextracted with DCM
  9. dry with materialThe organic phase is dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue is used without purification

Sources & evidence

ORD record
ord-cd9f7f0a16b548028d7610ecffa97ea6
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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