Triphenylphosphine → HCID 86685025, compound

HRID 921512Notes

Reaction equation

HRID 921512 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[Br-:1].[C:8]([O:7][C:6]([NH:5][CH2:4][CH2:3][CH2:2][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:12])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 86685025HCID 86685025, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tert-butyl (3-bromopropyl)carbamate (5.45 g, 22.88 mmol) and triphenylphosphine (6.0 g, 22.88 mmol) in 100 ml of acetonitrile was heated to reflux for 2 days. Upon cooling to room temperature, the compound was purified with silica chromatography using methylene chloride/methanol as an eluent to give a yield of 64% (6.15 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 days
  3. customthe compound was purified with silica chromatography
  4. customto give a yield of 64% (6.15 g)

Sources & evidence

ORD record
ord-87df036d0e9c48c68d38b19519fada87
Source dataset
uspto-grants-2016_03
Patent number
US09273343B2

Reaction notes

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