Diethyl Ether → HCID 54514658, compound

HRID 1432870Notes

Reaction equation

HRID 1432870 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11]O)=[CH:8][CH:9]=2)[N:4]([S:13]([C:16]2(C)[CH:21]=[CH:20]C=[CH:18][CH2:17]2)(=[O:15])=[O:14])[CH:3]=1.P(Br)(Br)[Br:24].CCO[CH2:30][CH3:31]>>[Br:24][CH2:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([Cl:1])=[CH:3][N:4]2[S:13]([C:16]2[CH:21]=[CH:20][C:30]([CH3:31])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 69026650HCID 69026650, compound

Product 1

HCID 54514658HCID 54514658, compound

Conditions

Temperature
0 °C

Procedure

To a solution of [3-chloro-1-(toluene-1-sulfonyl)-1H-indol-6-yl]-methanol (0.45 g, 1.34 mmol) in 13 mL of Et2O at 0° C. is added phosphorous tribromide (0.04 mL, 0.40 mmol). The mixture is stirred at 0° C. for 15 min, then at room temperature for 2 hours. The mixture is quenched by the addition of water/ice and diluted with Et2O. The layers are separated and the organic phase is washed with saturated NaHCO3 solution, water and saturated NaCl solution. The organic layer is dried over anhydrous MgSO4, filtered and concentrated to provide the title compound (0.47 g, 1.18 mmol) as an oil. The crude product is used in the subsequent step without further purification. 1H NMR (CDCl3, 300 MHz) δ8.09 (s, 1H), 7.79 (d, 2H), 7.59 (s, 1H), 7.50 (d, 1H), 7.35 (d, 1H), 7.27 (m, 2H), 4.66 (s, 2H), 2.39 (s, 3H).

Workup

  1. waitat room temperature for 2 hours
  2. customThe mixture is quenched by the addition of water/ice
  3. additiondiluted with Et2O
  4. customThe layers are separated
  5. washthe organic phase is washed with saturated NaHCO3 solution, water and saturated NaCl solution
  6. dry with materialThe organic layer is dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-73a3a2a8fe4746b6b1ac40db1ed587f6
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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