(Diethylamino)sulfur trifluoride → 5-Bromo-1-(1-fluoropropyl)-2,3-dimethoxybenzene

HRID 638946Notes

Reaction equation

HRID 638946 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5]([O:12][CH3:13])=[C:6]([CH:8](O)[CH2:9][CH3:10])[CH:7]=1.CCN(S(F)(F)[F:22])CC>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5]([O:12][CH3:13])=[C:6]([CH:8]([F:22])[CH2:9][CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 14470708HCID 14470708, compound

Product 1

HCID 686856045-Bromo-1-(1-fluoropropyl)-2,3-dimethoxybenzeneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-(5-bromo-2,3-dimethoxyphenyl)propan-1-ol (400 mg, 1.45 mmol) in DCM (10 mL) at −78° C. was added DAST (0.58 mL, 4.36 mmol) and stirred the reaction for 10 min at −78° C., then warmed to 0° C. for 2 h. The reaction was quenched with water and saturated aqueous NH4Cl (100 mL), extracted with EtOAc, dried over NasSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel using 30% EtOAc in hexanes as an eluent to furnish 5-bromo-1-(1-fluoropropyl)-2,3-dimethoxybenzene (80%).

Workup

  1. customthe reaction for 10 min at −78° C.
  2. customThe reaction was quenched with water and saturated aqueous NH4Cl (100 mL)
  3. extractionextracted with EtOAc
  4. customdried over NasSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography on silica gel using 30% EtOAc in hexanes as an eluent

Sources & evidence

ORD record
ord-6c80cc6a6fbe4320ae9c060d4bcdb4ec
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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