Phosphorus tribromide → 2-(Bromomethyl)-1-fluoro-4-iodobenzene, alpha-Bromo-2-fluoro-5-iodotoluene

HRID 1747222Notes

Reaction equation

HRID 1747222 reaction equation
P(Br)(Br)[Br:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:7]=1[CH2:13]O>C(Cl)Cl>[Br:2][CH2:13][C:7]1[CH:8]=[C:9]([I:12])[CH:10]=[CH:11][C:6]=1[F:5]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 22220046HCID 22220046, compound

Product 1

HCID 218745912-(Bromomethyl)-1-fluoro-4-iodobenzene, alpha-Bromo-2-fluoro-5-iodotoluene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Phosphorus tribromide 1.0 M soln. in DCM (18.9 mL, 18.9 mmol) was added dropwise to a 0° C. solution of (2-fluoro-5-iodo-phenyl)-methanol G-6 (9.52 g, 37.8 mmol) in DCM (215 mL) and the resulting mixture was stirred for 1 h before being quenched with water. The layers were separated and the aqueous phase was re-extracted with DCM (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by flash chromatography (eluting with 5% EtOAc in hexane) to give the title compound as a white solid. LC-MS B: tR=0.92 min; No ionisation; 1H NMR (DMSO) δH: 7.93 (dd, J1=7.1 Hz, J2=2.3 Hz, 1H), 7.74 (ddd, J1=8.6 Hz, J2=4.9 Hz, J3=2.3 Hz, 1H), 7.10 (dd, J1=10.0 Hz, J2=8.7 Hz, 1H), 4.66 (s, 2H).

Workup

  1. custombefore being quenched with water
  2. customThe layers were separated
  3. extractionthe aqueous phase was re-extracted with DCM (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give the crude product that
  9. customwas purified by flash chromatography (eluting with 5% EtOAc in hexane)

Sources & evidence

ORD record
ord-33df683e78954e399cd8dc29ac5d509b
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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