Triphenylphosphine → 2-Bromomethyl-1-(4-methylphenyl)sulfonyl-1H-indole

HRID 54847Notes

Reaction equation

HRID 54847 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.OC[CH2:24][C:25]1[N:26]([S:34]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)(=[O:36])=[O:35])[C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][CH:28]=2>C(Cl)Cl>[Br:20][CH2:24][C:25]1[N:26]([S:34]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)(=[O:36])=[O:35])[C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][CH:28]=2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 162030902-Hydroxyethyl-1-(4-methylphenyl)sulfonyl-1H-indole

Product 1

HCID 190478642-Bromomethyl-1-(4-methylphenyl)sulfonyl-1H-indoleYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of triphenylphosphine (20.2 g, 77 mmol) in dry CH2Cl2 (80 mL) was added dropwise a solution of bromine (11.9 g, 77 mmol) in dry CH2Cl2 (40 mL). The stirring was continued for one hour and then a solution of compound of step 2 (23.2 g, 77 mmol) in dry CH2Cl2 (40 mL) was added dropwise. The resulting mixture left stirring for 12 hours. After removing the solvent the residue was taken up in ethyl acetate and washed with water. The organic extract was dried over MgSO4 and the solvent evaporated in vacuo. The residue was chromatographed over silica gel using toluene as eluant to give a yellow oil (21.0 g, 75 %); IR (film) 1600 cm-1, MS ((70eV): m/z 363 (M+,12.6), 129 (100).

Workup

  1. waitThe resulting mixture left
  2. customAfter removing the solvent the residue
  3. washwashed with water
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. customthe solvent evaporated in vacuo
  7. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-950a0701ac2b43a595e361993291b0ec
Source dataset
uspto-grants-1997_04
Patent number
US05622983

Reaction notes

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