Boron tribromide → HCID 57925832, compound

HRID 1013457Notes

Reaction equation

HRID 1013457 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([P:9]2(=[O:16])[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:15][N:12]1[CH2:13][CH2:14][P:9]([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)(=[O:16])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57925863HCID 57925863, compound

Product 1

HCID 57925832HCID 57925832, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

4-(4-Methoxyphenyl)-1-methyl-1,4-azaphosphinane 4-oxide (1.05 g, 4.39 mmol) was made 0.16 M in DCM and stirred at −78° C. To this stirring solution was added BBr3 (2.09 g, 8.34 mmol) dropwise. The reaction mixture was slowly warmed to ambient temperature over 16 h. The precipitate was filtered off then dissolved in water. The pH was adjusted to pH=7 with 2N aq HCl. A precipitate was filtered off and the filtrate was concentrated in vacuo. The residue was suspended in 4:1 DCM:MeOH and stirred for 20 mins. The solids were filtered off and the filtrate was concentrated in vacuo to afford the requisite product. MS: cal'd 226 (MH+), exp 226 (MH+)

Workup

  1. temperatureThe reaction mixture was slowly warmed to ambient temperature over 16 h
  2. filtrationThe precipitate was filtered off
  3. dissolutionthen dissolved in water
  4. filtrationA precipitate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. stirringMeOH and stirred for 20 mins
  7. filtrationThe solids were filtered off
  8. concentrationthe filtrate was concentrated in vacuo
  9. customto afford the requisite product

Sources & evidence

ORD record
ord-01f1dc3e80594ee7a757b14e6364dafc
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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