Carbon tetrabromide → tert-Butyl 3-(bromomethyl)phenylcarbamate

HRID 1616167

Reaction equation

HRID 1616167 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:37]>ClCCl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][Br:37])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 14523557tert-Butyl (3-(hydroxymethyl)phenyl)carbamate

Product 1

HCID 14523558tert-Butyl 3-(bromomethyl)phenylcarbamateYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[3-(hydroxymethyl)phenyl]carbamate (0.90 g, 4.0 mmol) in dichloromethane (15 mL) cooled at 0° C. was added triphenylphosphine (1.59 g, 6.05 mmol) and carbon tetrabromide (2.01 g, 6.05 mmol) and the reaction was stirred at rt overnight. The reaction was quenched with water and extracted with DCM (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 20% EtOAc/hexanes) to afford tert-butyl[3-(bromomethyl)phenyl]carbamate (0.82 g, 70%). LC-MS: (FA) ES+ 271.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with DCM (2×)
  3. washThe combined organic phases were then washed with water, and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash silica gel chromatography (0% to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6f3da6370e4c4d2e9cd49559445134a6
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Linked notes

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