Dichloromethane → 3-(2-bromoethyl)-5-fluoro-1H-indole

HRID 1095499Notes

Reaction equation

HRID 1095499 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(Cl)Cl.[Br:17]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O>[Br:17][CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[NH:7][CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 136162482-(5-fluoro-1H-indol-3-yl)ethanol

Product 1

HCID 112072263-(2-bromoethyl)-5-fluoro-1H-indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(5-Fluoro-1H-indol-3-yl)-ethanol (20.0 g, 112 mmol) was dissolved in abs. CH2Cl2 (250 ml), and tetrabromomethane (56.0 g, 170 mmol) was added at RT. Triphenylphosphine (44.0 g, 165 mmol) was then added in portions at RT, while cooling with water. The solution was stirred at RT for 2.5 h and then concentrated i. vac. The residue was absorbed on to silica gel and divided into two equal portions. The crude product was purified by flash chromatography over 2 columns each with 500 g of silica gel and cyclohexane/ethyl acetate (9:1→4:1). Yield: 25.4 g (93%), red solid

Workup

  1. concentrationconcentrated i
  2. customThe residue was absorbed on to silica gel
  3. customThe crude product was purified by flash chromatography over 2 columns each with 500 g of silica gel and cyclohexane/ethyl acetate (9:1→4:1)

Sources & evidence

ORD record
ord-7a188eeb2919446985df2171ccd48f63
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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