(Diethylamino)sulfur trifluoride → 2-Bromo-1-(2-fluoroethoxy)-4-nitrobenzene

HRID 1107290Notes

Reaction equation

HRID 1107290 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10]O.C(N(S(F)(F)[F:21])CC)C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][F:21]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 187870553-Bromo-4-(2-hydroxy)ethoxy Nitrobenzene

Product 1

HCID 177499862-Bromo-1-(2-fluoroethoxy)-4-nitrobenzeneYield 15.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (-78° C.) suspension of 3-Bromo-4-(2-hydroxy)ethoxy nitrobenzene (7.9 g, 30 mmol) in dichoromethane (80 ml) was added diethylaminosulphur trifluoride (3.88 ml, 31.5 mmol). The solution was stirred at ambient temperature for 2 hours, then quenched by the dropwise addition of water (100 ml). The organic layer was separated, washed with brine (100 ml), dried (MgSO4), and evaporated in vacuo. Purification on silica, eluting with 15%-20% ethyl acetate in hexane afforded the title compound as a yellow oil (1.2 g, 15%). 1H NMR (250 MHz, CDCl3) δ 4.35 (1H, dd, J=4.1 Hz, J=2.4 Hz), 4.45 (1H, dd, J=2.4 Hz, J=4.1 Hz), 4.75 (1H, dd, J=4 Hz, J=5.8 Hz), 4.95 (1H, dd, J=4 Hz, J=5.8 Hz), 6.98 (1H, d, J=9.1 Hz), 8.21 (1H, dd, J=2.7 Hz, J=9 Hz).

Workup

  1. temperatureTo a cooled
  2. customquenched by the dropwise addition of water (100 ml)
  3. customThe organic layer was separated
  4. washwashed with brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customPurification on silica
  8. washeluting with 15%-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-180cdc40a85f4a93bc5e1b9093df5bb3
Source dataset
uspto-grants-2000_05
Patent number
US06060469

Reaction notes

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