Water → tert-Butyl [2-(bromomethyl)phenyl]carbamate

HRID 2356668Notes

Reaction equation

HRID 2356668 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].P(Br)(Br)[Br:18].C(=O)([O-])O.[Na+].O>ClCCl>[Br:18][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 15292992tert-Butyl [2-(hydroxymethyl)phenyl]carbamate

Product 1

HCID 10469205tert-Butyl [2-(bromomethyl)phenyl]carbamateYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

1.3 g of tert-butyl (2-hydroxymethylphenyl)carbamate were dissolved in 20 ml of dichloromethane; at 5° C., a solution of 630 mg of phosphorus tribromide in 5 ml of DCM was then added dropwise. The reaction mixture was subsequently stirred at 5° C. for 2 h. For workup, the mixture was admixed cautiously with solid sodium hydrogencarbonate and 1 ml of water, stirred at 5° C. for 30 min, filtered through a cartridge and concentrated under reduced pressure. tert-Butyl (2-bromomethylphenyl)carbamate was obtained in a 67% yield. 1H NMR: 8.71, s, 1H, 7.45, d, 1H, 7.42, d, 1H, 7.3, t, 1H, 7.1, t, 1H; 4.78, 2, 2H, 1.45, s, 9H.

Workup

  1. stirringstirred at 5° C. for 30 min
  2. filtrationfiltered through a cartridge
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a75e1f2dcbc4049b4d64bd55035c30f
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

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