Phosphorus tribromide → HCID 57429690, compound

HRID 420286Notes

Reaction equation

HRID 420286 reaction equation
P(Br)(Br)[Br:2].[CH2:5]([O:12][C:13](=[O:24])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][C:16]=1[F:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CCOCC>[CH2:5]([O:12][C:13](=[O:24])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][Br:2])=[CH:17][C:16]=1[F:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromide2×HCID 66649617HCID 66649617, compound

Product 1

HCID 57429690HCID 57429690, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Phosphorous tribromide (20.9 mL, 218 mmol) was added to diethylether (700 mL) at 0° C. To the PBr3 solution was added dropwise (2-fluoro-4-hydroxymethyl-phenyl)-carbamic acid benzyl ester (36.5 g, 133 mmol) in Et2O (400 mL) at 0° C. over 1 h. The reaction mixture was stirred at room temperature for 45 min and was carefully quenched at 0° C. with MeOH (100 mL). The reaction mixture was diluted with aq. NaHCO3 solution and extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated to provide the title compound as a yellow foam: TLC (cyclohexane-EtOAc 1:1) Rf=0.88; HPLC RtI=1.16 min; 1H NMR (360 MHz, CDCl3): δ 8.13 (t, 1H), 7.48-0.37 (m, 5H), 7.21-7.14 (m, 2H), 6.78 (s broad, 1H), 5.25 (s, 2H), 4.47 (s, 2H).

Workup

  1. customwas carefully quenched at 0° C. with MeOH (100 mL)
  2. additionThe reaction mixture was diluted with aq. NaHCO3 solution
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-365bb718099842198e589241dbab5d9c
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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