Acetic Acid → HCID 21901952, compound

HRID 1160366Notes

Reaction equation

HRID 1160366 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:13](=[O:15])[CH3:14])[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(O)(=O)C.[Br:22]Br.O>CO>[Br:22][CH2:14][C:13]([C:9]1([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:16])([F:17])[F:1])=[CH:8][CH:7]=2)[CH2:10][CH2:11][CH2:12]1)=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 24408BromineHCID 219019801-(1-(4-(Trifluoromethyl)phenyl)cyclobutyl)ethanone

Product 1

HCID 21901952HCID 21901952, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1-[1-(4-Trifluoromethyl-phenyl)-cyclobutyl]-ethanone (1.06 g) in methanol (8 mL) was cooled to 0° C. Acetic acid containing 30% HBr (0.35 mL) was added, and then precisely 1 molar equivalent of bromine was added dropwise. The reaction mixture was maintained at 0° C. overnight, poured into 20 mL of water, and extracted with ether. The extracts were dried, filtered, concentrated, and purified on silica gel to give pure 2-bromo-1-[1-(4-trifluoromethyl-phenyl)-cyclobutyl]-ethanone (1.12 g, 80%). Data for this bromoketone: MS 321 (M); 1H NMR (300 MHz, CDCl3) δ 7.82 (d, 8 Hz, 2H), 7.39 (d, 8 Hz, 2H), 3.82 (s, 2H), 2.80-2.95 (m, 2H), 2.45-2.60 (m, 2H), 1.90-2.10 (m, 2H).

Workup

  1. extractionextracted with ether
  2. customThe extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on silica gel

Sources & evidence

ORD record
ord-29f038e7d3814b9ba9f2665c5460bf53
Source dataset
uspto-grants-2010_10
Patent number
US07816375B2

Reaction notes

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