Dimethyl Sulfide → [4-Iodo-3-(naphthalen-2-yloxy)-phenyl]-methyl bromide

HRID 379040Notes

Reaction equation

HRID 379040 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][C:3]=1[O:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1.[Br:21]N1C(=O)CCC1=O.CSC>C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:21])=[CH:4][C:3]=1[O:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 67184N-bromobutanimideHCID 21697102[4-Iodo-3-(naphthalen-2-yloxy)-phenyl]-methanol

Product 1

HCID 21696995[4-Iodo-3-(naphthalen-2-yloxy)-phenyl]-methyl bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-iodo-3-(naphthalen-2-yloxy)-phenyl]-methanol (0.085 g, 0.226 mmol) in CH2Cl2 (2 mL) at −15° C. was added a cold (0° C.) solution of N-bromosuccinimide (0.120 g, 0.68 mmol) in dimethyl sulfide (0.060 mL, 0.814 mmol) with stirring. The reaction mixture was allowed to warm to ambient temperature overnight, concentrated to dryness, and chromatographed (SiO2, 10% EtOAc:hexane) to give the title compound which was used without purification.

Workup

  1. concentrationconcentrated to dryness
  2. customchromatographed (SiO2, 10% EtOAc:hexane)

Sources & evidence

ORD record
ord-1d0e4b4c1d104fe6bc6b9e173c13e015
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

Loading…