Carbon tetrabromide → 3-(2-bromoethyl)-5-fluoro-1H-indole
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12]O.C(Br)(Br)(Br)[Br:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][Br:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 5-fluoro-3-(2-hydroxyethyl)indole (10.3 g, 0.056 mole) and CBr4 (24.8 g, 0.073 mole) in 100 mL of dry acetonitrile at 0° C. under Ar was added a solution of triphenylphosphine (19.6 g, 0.073 mole) in 200 mL of dry acetonitrile. The mixture was stirred at 0° C. for 1 h and then at room temperature for 2 h. The resulting mixture was evaporated and the residue was chromatographed (SiO2 /ethyl acetate-hexane=1:4) to give the product (8.50 g, 61%) as a brown solid; IR (neat) 3440 cm-1 ; 1Hnmr (80 MHz, CDCl3) δ: 7.75 (br s, 1H), 7.15-6.57 (m, 4H), 3.53-3.32 (m, 2H), 3.17-2.94 (m, 2H).
Workup
- waitat room temperature for 2 h
- customThe resulting mixture was evaporated
- customthe residue was chromatographed (SiO2 /ethyl acetate-hexane=1:4)
Sources & evidence
- ORD record
- ord-c661b5b60f89429a95731592da71b372
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05077293
Reaction notes
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