Tert-Butylamine → HCID 67346586, compound

HRID 1669477Notes

Reaction equation

HRID 1669477 reaction equation
C(N)(C)(C)C.[Br:6]Br.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1.C(Cl)Cl.CCOCC.O>[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Br:6])[C:17]=1[OH:22])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 3

HCID 6385Tert-ButylamineHCID 24408BromineHCID 804592-Benzyloxyphenol

Product 1

HCID 67346586HCID 67346586, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

Tert-butyl amine (2 eq) was dissolved in toluene (1M) and the solution was cooled to −30° C. Br2 (1 eq) was added dropwise maintaining the temperature. The mixture was left stirring for 30 min, then it was cooled to −78° C. A solution of 2-benzyloxyphenol (1 eq) in DCM (6M) was added dropwise. The mixture was allowed to reach RT over the course of 3 h. The mixture was diluted with Et2O and H2O was added. The mixture was washed with 1N HCl, sat. aq. Na2S2O3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. The residue was purified by FC (PE:EtOAc, 9:1). The colourless oil was used without further characterization in the next reaction. (ES−) m/z 277, 279 (M−H)−.

Workup

  1. temperaturemaintaining the temperature
  2. waitThe mixture was left
  3. temperatureit was cooled to −78° C
  4. customto reach RT over the course of 3 h
  5. additionwas added
  6. washThe mixture was washed with 1N HCl, sat. aq. Na2S2O3 and brine
  7. dry with materialAfter drying over Na2SO4 all volatiles
  8. customwere evaporated in vacuo
  9. customThe residue was purified by FC (PE:EtOAc, 9:1)
  10. customThe colourless oil was used without further characterization in the next reaction

Sources & evidence

ORD record
ord-ed42c8da1d974888b95032826daae174
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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