Carbon tetrabromide → HCID 86699391, compound

HRID 1777553Notes

Reaction equation

HRID 1777553 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])=[C:5]2[CH2:19][CH2:20]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:41]C(Br)(Br)Br>C1COCC1>[Br:41][CH2:20][CH2:19][C:5]1[C:4]2[C:8](=[CH:9][C:10]([Cl:11])=[C:2]([Cl:1])[CH:3]=2)[NH:7][C:6]=1[Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 679733232-(5,6-Dichloro-2-(triethylsilyl)-1H-indol-3-yl)ethanol

Product 1

HCID 86699391HCID 86699391, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(5,6-dichloro-2-(triethylsilyl)-1H-indol-3-yl)ethanol (1.7 g; 4.94 mmol) in THF (6 mL) was added to a solution of triphenylphosphine (2.59 g; 9.87 mmol) and perbromomethane (3.27 g; 9.87 mmol) in THF (40 mL) pre-stirred for 30 minutes. The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was then filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 0.548 g (27%) of the title compound as a brown oil.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 18 hours
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-4ac7b0692eb54dd3a99e9a6683e2b8c9
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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