Phosphorus tribromide → HCID 58066671, compound

HRID 390415Notes

Reaction equation

HRID 390415 reaction equation
[C:1]([S:5][CH2:6][C:7]1[CH:8]=[C:9]([NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=[CH:11][C:12]=1[CH2:13]O)([CH3:4])([CH3:3])[CH3:2].P(Br)(Br)[Br:23]>COCCOC>[Br:23][CH2:13][C:12]1[CH:11]=[CH:10][C:9]([NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:8][C:7]=1[CH2:6][S:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 58066680HCID 58066680, compound

Product 1

HCID 58066671HCID 58066671, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

To N-(3-tert-butylsulfanylmethyl-4-hydroxymethyl-phenyl)-2,2-dimethyl-propionamide (1.6 g, 5.17 mmol) in DME (60 mL) at 0° C. was added phosphorus tribromide (0.54 mL, 5.69 mmol) slowly via syringe. The reaction was stirred at 0° C. for 20 minutes, until no starting material was seen by analytical tlc. The mixture was quenched with H2O and diluted with EtOAc (300 mL) and H2O (100 mL). The organic layer was separated and washed with H2O, and then dried, filtered, and concentrated to give the title compound.

Workup

  1. customThe mixture was quenched with H2O
  2. additiondiluted with EtOAc (300 mL) and H2O (100 mL)
  3. customThe organic layer was separated
  4. washwashed with H2O
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3f36d9d0bb744d829f30093304e0c20e
Source dataset
uspto-grants-2013_02
Patent number
US08383654B2

Reaction notes

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