Carbon tetrabromide → HCID 23045078, compound

HRID 2108032Notes

Reaction equation

HRID 2108032 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]#[C:32][CH2:33][CH2:34][CH2:35]O.C(Br)(Br)(Br)[Br:38]>ClCCl>[Br:38][CH2:35][CH2:34][CH2:33][C:32]#[C:31][CH2:30][O:29][CH2:28][CH2:27][CH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 23045064HCID 23045064, compound

Product 1

HCID 23045078HCID 23045078, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (2.89 g) in dichloromethane (20 ml) was added dropwise to a solution of 6-[3-(2-pyridinyl)propoxy]-4-hexyn-1-ol (2.33 g) and carbon tetrabromide (3.65 g) in dichloromethane (30 ml) cooled in an ice-bath. The reaction mixture was stirred at room temperature for 1 h, the solvent was evaporated and the residue was purified by FCC eluting with hexane-ether (1:1) to give the title compound as an orange oil (2.0 g), t.l.c. (hexane-ether 1:1) Rf 0.2.

Workup

  1. temperaturecooled in an ice-bath
  2. customthe solvent was evaporated
  3. customthe residue was purified by FCC
  4. washeluting with hexane-ether (1:1)

Sources & evidence

ORD record
ord-b75984e03be840d8a7bf0608b204e170
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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