Phosphorus tribromide → tert-Butyl 3-(1-bromoethyl)phenylcarbamate

HRID 2175259Notes

Reaction equation

HRID 2175259 reaction equation
O[CH:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1)[CH3:3].[Br:18]P(Br)Br>C(Cl)Cl.C1COCC1>[Br:18][CH:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1)[CH3:3]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 16740724tert-butyl N-[3-(1-hydroxyethyl)phenyl]carbamate

Product 1

HCID 86712586tert-Butyl 3-(1-bromoethyl)phenylcarbamateYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of tert-butyl 3-(1-hydroxyethyl)phenylcarbamate (5.8 g, 24.44 mmol) in CH2Cl2 (30 mL) and THF (20 mL) at 0° C. was added tribromophosphine (1 M solution in CH2Cl2, 24.44 mL, 24.44 mmol). The reaction was stirred at 0-10° C. for 1.5 h and then quenched with water. The mixture was extracted with CH2Cl2. The organic layer was washed with saturated NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated to afford the title compound (5.7 g, 78% yield) as a colorless oil. LCMS, [M+Na]+=322.1.

Workup

  1. customquenched with water
  2. extractionThe mixture was extracted with CH2Cl2
  3. washThe organic layer was washed with saturated NaHCO3 and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-64a6a54f2b4940b1847a406c162fb8b2
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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