Carbon tetrabromide → HCID 15228264, compound

HRID 1769638Notes

Reaction equation

HRID 1769638 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:20]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][CH:27]=[C:26]2[CH2:32][CH2:33]O)([O-:22])=[O:21].C(Br)(Br)(Br)[Br:36]>C(#N)C.C(OCC)(=O)C>[N+:20]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][CH:27]=[C:26]2[CH2:32][CH2:33][Br:36])([O-:22])=[O:21]

Participants

6

Reactant 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 119705002-(5-Nitro-1H-indol-3-yl)ethan-1-ol

Product 1

HCID 15228264HCID 15228264, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of triphenylphosphine (2.83 g, 0.011 mol) in 100 mL of acetonitrile was added a solution of 5-nitro-3-(2-hydroxyethyl)indole (2.00 g, 0.0097 mol) in 25 mL of acetonitrile, followed by a solution of CBr4 (3.60 g, 0.011 mol) in 25 mL of acetonitrile, at 0° C. under Ar. The mixture was stirred at room temperature for 18 h and then another 0.283 g (1.1 mmol) of triphenylphosphine and 0.360 g (1.1 mmol) of CBr4 were added. After 2.5 h the mixture was diluted with ethyl acetate, washed (H2O, brine), dried (Na2SO4) and evaporated and the residue was chromatographed (SiO2 /ethyl acetate-hexane, 1:4) to give the title compound (2.27 g, 87%) as a yellow solid: IR (neat) 3370, 1334 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ11.69 (s, 1H), 8.60 (d, J=2.1 Hz, 1H), 7.98 (dd, J=9.0, 2.2 Hz, 1H), 7.54-7.49 (m, 2H), 3.76 (t, J=7.2 Hz, 2H), 3.32 (t, J=7.2 Hz, 2H).

Workup

  1. washwashed (H2O, brine)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customthe residue was chromatographed (SiO2 /ethyl acetate-hexane, 1:4)

Sources & evidence

ORD record
ord-5fdf306e4757423587c9393b257651ed
Source dataset
uspto-grants-1995_01
Patent number
US05382592

Reaction notes

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