Reaktion #1483106

ord-613b8f625c524b7da8c537f18eaf0267

Reaktionsgleichung

CC(Br)C(=O)Br
2-bromopropionyl bromide
CC(Br)C(=O)Br
2-bromo propionyl bromide
CCCCCCCCCCCC(C)(C)O
2-methyltridecan-2-ol
CCN(CC)CC
triethylamine
CCCCCCCCCCCC(C)(C)OC(=O)C(C)Br
74
Ausbeute 61.3%
CCCCCCCCCCCC(C)(C)OC(=O)C(C)Br
2-methyltridecan-2-yl 2-bromopropanoate
Ausbeute 61.3%

Lösungsmittel

Reaktionsbedingungen

Temperatur
57.5°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction mixture was quenched with saturated sodium bicarbonate solution
  2. 2
    workup.STIRRINGstirred for 15 minutes at 25-35° C
  3. 3
    SonstigeThe aqueous and organic layers were separated
  4. 4
    Waschenthe organic layer was washed with brine
  5. 5
    Waschenthe combined organic layers were washed with brine solution
  6. 6
    TrocknenThe organic layer was dried over Na2SO4
  7. 7
    Einengenconcentrated under vacuum

Vorschrift

To a stirred solution of 2-methyltridecan-2-ol 73 (5 g, 23.4 mmol) in Toluene (50 mL) was added triethylamine (3.29 mL, 23.4 mmol)) and followed by 2-bromopropionyl bromide 58 (5.11 g, 23.7 mmol) at 5-10° C. The reaction mixture was stirred for 3 hours at 55-60° C.; the reaction was monitored by TLC. The reaction mixture was quenched with saturated sodium bicarbonate solution and stirred for 15 minutes at 25-35° C. The aqueous and organic layers were separated, the organic layer was washed with brine, and the combined organic layers were washed with brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 74 (5 g, yield: 61.27%) as a liquid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08900625B2uspto-grants-2014_12