Carbon tetrabromide → tert-Butyl N-(2-bromoethyl)carbamate

HRID 1454355Notes

Reaction equation

HRID 1454355 reaction equation
[C:1]([NH:8][CH2:9][CH2:10]O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[C:1]([NH:8][CH2:9][CH2:10][Br:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 4103526tert-Butyl N-(2-bromoethyl)carbamateYield 790%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To an ice-cooled solution of (N-Boc)-2-aminoethanol (2.5 g, 15.5 mmol) and carbon tetrabromide (7.5 g, 22.7 mmol) in dry benzene (25 ml), was added triphenyl phosphine (4.7 g, 17.9 mmol) in small portions over 10-15 min. After 30 min. solvent was evaporated and the product immediately purified by silica gel column chromatography to get (N-Boc)-2-aminoethylbromide (5.53 g, 790%).

Workup

  1. customAfter 30 min. solvent was evaporated
  2. customthe product immediately purified by silica gel column chromatography

Sources & evidence

ORD record
ord-79dbcfb49ca245ea846b83a6e20d8e1f
Source dataset
uspto-grants-2009_01
Patent number
US07479536B1

Reaction notes

Loading…