Phosphorus tribromide → 2-(Bromomethyl)-5-(methylsulphonyl)benzotrifluoride

HRID 1949354Notes

Reaction equation

HRID 1949354 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11]O)=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1)(=[O:4])=[O:3].P(Br)(Br)[Br:18]>C(Cl)Cl>[Br:18][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][C:7]=1[C:13]([F:16])([F:15])[F:14]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 66936507(4-(Methylsulfonyl)-2-(trifluoromethyl)phenyl)methanol

Product 1

HCID 513420492-(Bromomethyl)-5-(methylsulphonyl)benzotrifluorideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Methanesulfonyl-2-trifluoromethyl-phenyl)-methanol (4.87 mmol) was dissolved in 40 mL of CH2Cl2 and the resulting solution was treated with PBr3 (1 N, 4.87 mL) at 0° C. for 4 h. The mixture was partitioned between CH2Cl2 and water. The combined CH2Cl2 extracts were washed with brine, dried and evaporated. The residue was purified by flash column chromatography on silica gel (heptane/EtOAc 3:1 v/v) to afford white crystals (1.24 g, 80%).

Workup

  1. customThe mixture was partitioned between CH2Cl2 and water
  2. washThe combined CH2Cl2 extracts were washed with brine
  3. customdried
  4. customevaporated
  5. customThe residue was purified by flash column chromatography on silica gel (heptane/EtOAc 3:1 v/v)

Sources & evidence

ORD record
ord-327d33c9ab8d49b2b30e3f2d2fd8001d
Source dataset
uspto-grants-2013_03
Patent number
US08399681B2

Reaction notes

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