Hydrochloric Acid → 4-[(4-Bromo-phenoxy)-difluoro-methyl]-cyclohexanone

HRID 84305Notes

Reaction equation

HRID 84305 reaction equation
Cl.[Br:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]([F:20])([F:19])[CH:9]2[CH2:18][CH2:17][C:12]3(OCC[O:13]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1>CC(C)=O>[Br:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]([F:19])([F:20])[CH:9]2[CH2:10][CH2:11][C:12](=[O:13])[CH2:17][CH2:18]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 672495298-((4-Bromophenoxy)difluoromethyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 672502664-[(4-Bromo-phenoxy)-difluoro-methyl]-cyclohexanoneYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4 N HCl (4.23 mL, 16.9 mmoles) was added to a solution of 8-((4-bromophenoxy)difluoromethyl)-1,4-dioxaspiro[4.5]decane (1230 mg, 3.387 mmoles) in acetone (11.3 mL, 0.3M) and was allowed to stir overnight at room temperature. The reaction mixture was concentrated onto silica gel and purified via chromatography (9:1 heptane:ethyl acetate to 3:7 heptane:EtOAc over 40 minutes followed by 100% EtOAc for 10 minutes) afforded the desired material (1081 mg, 97.13%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.27 (br. s., 2 H) 1.39-1.51 (m, 2 H) 1.96-2.10 (m, 5 H) 3.32-3.38 (m, 0 H) 3.47-3.55 (m, 1 H) 7.05-7.13 (m, 2 H) 7.45-7.53 (m, 2 H)

Workup

  1. concentrationThe reaction mixture was concentrated onto silica gel
  2. custompurified via chromatography (9:1 heptane:ethyl acetate to 3:7 heptane:EtOAc over 40 minutes followed by 100% EtOAc for 10 minutes)

Sources & evidence

ORD record
ord-cb5839e71aaf41adbc9456cca8c2dee6
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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