Water → HCID 57435890, compound

HRID 30581Notes

Reaction equation

HRID 30581 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]O)[CH:5]=[CH:6][CH:7]=1.C(N(S(F)(F)[F:20])CC)C.O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][F:20])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 57435887931430-20-5

Product 1

HCID 57435890HCID 57435890, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-(3-bromophenyl)pentan-1-ol (0.63 g, 2.6 mmol) in methylene chloride at −78° C. was treated with a solution of diethylamino sulfur trifluoride (DAST) (0.7 mL, 5.2 mmol) in methylene chloride, allowed to warm to room temperature, stirred for 0.5 h at room temperature, poured into water and extracted with ether. The extracts were combined washed sequentially with saturated sodium bicarbonate and water, dried over magnesium sulfate and concentrated under reduced pressure. The concentrate was purified by flash chromatography on silica gel, 40:1 hexane/ethyl acetate as eluent to give 1-bromo-3-(5-fluoropentyl)benzene as a pale yellow oil, 0.4 g (63% yield); 1H NMR (DMSO-d6) δ 1.3 (m, 2H); 1.6 (m, 4H); 2.5 (t, 2 H); 4.4 (dxt, 2H); 7.2 (m, 2 H); 7.4 (m, 2 H); MS [(+)ESI] m/z=245 [M−H]+.

Workup

  1. extractionextracted with ether
  2. washThe extracts were combined washed sequentially with saturated sodium bicarbonate and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by flash chromatography on silica gel, 40:1 hexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-edecd3fd90264d50b6719419c29acc58
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

Loading…