Triphenylphosphine → tert-Butyl (4-(2-bromoethyl)phenyl)carbamate

HRID 633724Notes

Reaction equation

HRID 633724 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:25][CH:24]=1.[Br:37]N1C(=O)CCC1=O>ClCCl.CCOCC>[Br:37][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 11413715N-Boc-2-(4-aminophenyl)ethanol

Product 1

HCID 24800457tert-Butyl (4-(2-bromoethyl)phenyl)carbamateYield 69.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

8.68 g (33.08 mmol) of triphenylphosphine are added, under an argon atmosphere, to a solution of 7.85 g (33.08 mmol) of tert-butyl [4-(2-hydroxyethyl)phenyl]carbamate in 85 mL of dichloromethane. The mixture is cooled to 0° C. and 5.95 g (33.08 mmol) of N-bromosuccinimide are added portionwise over 25 minutes. Stirring is continued for 3 hours at 0° C. The solvent is then evaporated off, the oil obtained is taken up in ether and the precipitate formed is filtered off and discarded. The filtrate is evaporated and the residue is purified by chromatography on silica gel (eluent: 10/90 EtOAc/heptane) to give 6.90 g of tert-butyl [4-(2-bromoethyl)phenyl]carbamate, the characteristics of which are as follows:

Workup

  1. customThe solvent is then evaporated off
  2. customthe oil obtained
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. customThe filtrate is evaporated
  6. customthe residue is purified by chromatography on silica gel (eluent: 10/90 EtOAc/heptane)

Sources & evidence

ORD record
ord-9e3ba070fc454b869b3c9942eca52cf1
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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