Boron tribromide → HCID 58542237, compound

HRID 2067906Notes

Reaction equation

HRID 2067906 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([O:16]C)[CH:10]=2)=[N:6][CH:7]=1.B(Br)(Br)Br>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[Br:1][C:2]1[CH:7]=[N:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([OH:16])[CH:10]=2)=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 58542238HCID 58542238, compound

Product 1

HCID 58542237HCID 58542237, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a solution of 5-bromo-N-(4-fluoro-3-methoxyphenyl)pyrimidin-2-amine 44 (0.25 mmol) in 3 mL of anhydrous DCM at 0° C. is added BBr3 (1.27 mmol) drop wise. The reaction mixture is stirred at rt for 12 h. After this time the reaction mixture is diluted with a 2M solution of Na2CO3 and extracted with DCM (2×20 mL). The organic layer is washed with brine, dried over Na2SO4 and concentrated to afford 5-(5-bromopyrimidin-2-ylamino)-2-fluorophenol 45 as brownish solid which is used without further purification. MS (m/z) (M+1)+: 286.2.

Workup

  1. extractionextracted with DCM (2×20 mL)
  2. washThe organic layer is washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5057ac46cef4402cbd54e3fd8206d7c2
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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