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

HRID 1184012Notes

Reaction equation

HRID 1184012 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., 2H) 1.39-1.51 (m, 2H) 1.96-2.10 (m, 5H) 3.32-3.38 (m, OH) 3.47-3.55 (m, 1H) 7.05-7.13 (m, 2H) 7.45-7.53 (m, 2H)

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-02ee66c841cc4110a618c2e555275cf1
Source dataset
uspto-grants-2014_03
Patent number
US08664401B2

Reaction notes

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