Hydrochloric Acid → HCID 767785, compound

HRID 2273042Notes

Reaction equation

HRID 2273042 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([CH:11]2[CH2:16][CH2:15][CH:14]([C:17](=[O:19])[CH3:18])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Br[CH2:21][C:22](Br)=[O:23].Cl>C(Cl)Cl>[C:17]([CH:14]1[CH2:15][CH2:16][CH:11]([C:5]2[CH:10]=[CH:9][C:8]([C:22](=[O:23])[CH3:21])=[CH:7][CH:6]=2)[CH2:12][CH2:13]1)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) ChlorideHCID 1288374921060-31-12×

Product 1

HCID 767785HCID 767785, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Referring to Scheme 2-7 to a suspension of AlCl3 (1.58 g, 12 mmol) in DCM (30 mL) at −78° C. was added 1-(4-phenylcyclohexyl)ethanone (A1′) (1 g in DCM, 5.0 mmol), and bromoacetyl bromide (0.65 mL, 7.5 mmol) dropwise over 10 min. The mixture was stirred to rt for 15 min and heated at 40-50° C. for 3 h, cooled to rt and poured into a mixture of ice and HCl (1N). The organic layer was collected, and the aqueous layer was extracted with ethyl acetate (3×). The combined organic layers were concentrated on rotovap and purified silica gel column chromatography (Hexanes/EtOAc=8/2 (v/v)) to give the desired trans-isomer A2′ (1 g, 62% yield) along with a small amount of cis-isomer.

Workup

  1. temperatureheated at 40-50° C. for 3 h
  2. temperaturecooled to rt
  3. customThe organic layer was collected
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  5. concentrationThe combined organic layers were concentrated on rotovap
  6. custompurified silica gel column chromatography (Hexanes/EtOAc=8/2 (v/v))

Sources & evidence

ORD record
ord-d98e14bf44e049ba81343c18dc90e739
Source dataset
uspto-grants-2015_09
Patent number
US09120779B2

Reaction notes

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