Diethyl Ether → HCID 19430927, compound

HRID 1440351Notes

Reaction equation

HRID 1440351 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([CH2:19]O)[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Br)(Br)(Br)[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C>C(Cl)Cl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([CH2:19][Br:22])[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21258560HCID 21258560, compound

Product 1

HCID 19430927HCID 19430927, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.78 g (2.71 mmol) of alcohol (30) and 1.13 g (3.41 mmol) of carbontetrabromide in 10 ml of CH2Cl2 at 0° C. was added 1.07 g (4.08 mmol) of triphenylphosphine. After one hour at 0° C., the solvent was removed under reduced pressure. The residue was flash chromatographed on silica, eluting CH2Cl2. After trituration with diethyl ether there was obtained 0.82 g (80% yield) of 1-benzenesulfonyl-4-bromomethyl-1H-indole (31) as a white solid, m.p. 127°-128° C.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customchromatographed on silica
  3. washeluting CH2Cl2

Sources & evidence

ORD record
ord-0f7ff0ef87514843a4685fdf13425d63
Source dataset
uspto-grants-1996_03
Patent number
US05498727

Reaction notes

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