Acetic Acid → HCID 89225180, compound

HRID 2274530Notes

Reaction equation

HRID 2274530 reaction equation
[F:1][C:2]([F:16])([O:6][C:7]1[CH:8]=[C:9]([C:13](=[O:15])[CH3:14])[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4].C(O)(=O)C.[Br:21]Br>C(OCC)C.C(Cl)Cl>[Br:21][CH2:14][C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:2]([F:16])([F:1])[CH:3]([F:4])[F:5])[CH:8]=1)=[O:15]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 716505571-[3-(1,1,2,2-Tetrafluoroethoxy)phenyl]ethanone

Product 1

HCID 89225180HCID 89225180, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

1-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]ethanone (6.1 g, 25.8 mmol) was dissolved in diethyl ether (36.9 mL), and acetic acid (44.4 mL, 775 mmol) was added, followed by bromine (1.397 mL, 27.1 mmol). The reaction was stirred at 25° C. for 3 hours, then was diluted with DCM and extracted with saturated sodium bicarbonate solution. The combined organic layers were dried with anhydrous MgSO4, filtered, and concentrated. The crude product was purified on a silica gel column with a 340 g cartridge, using a 10% EtOAc/Hexanes isocratic mobile phase. 2-Bromo-1-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]ethanone (5 g, 15.87 mmol) was obtained. 1H NMR (400 MHz, CDCl3) 84.45 (s, 2H), 5.96 (t, J=53, 2.7 Hz, 1H), 7.47 (d, J=8.2 Hz, 1H), 7.55 (t, J=7.9 Hz, 1H), 7.83 (s, 1H), 7.91 (d, J=7.7 Hz, 1H).

Workup

  1. extractionextracted with saturated sodium bicarbonate solution
  2. dry with materialThe combined organic layers were dried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified on a silica gel column with a 340 g cartridge

Sources & evidence

ORD record
ord-2aebbea1826f4cf1b59e35776231b542
Source dataset
uspto-grants-2015_09
Patent number
US09126976B2

Reaction notes

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