Hydrochloric Acid → HCID 178521542, compound

HRID 715577Notes

Reaction equation

HRID 715577 reaction equation
FC1C=CC=CC=1C([O:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=O.[OH-].[Na+].Cl>CO>[Br:19][C:16]1[CH:15]=[CH:14][C:13]([C@@H:10]2[CH2:11][CH2:12][C@H:7]([OH:6])[CH2:8][CH2:9]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178525691HCID 178525691, compound

Product 1

HCID 178521542HCID 178521542, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

(cis)-4-(4-Bromophenyl)cyclohexyl 2-fluorobenzoate (110 mg) is dissolved in methanol (2 mL), treated with aqueous NaOH solution (1 M, 875 μL) and the mixture is stirred for 48 hours at room temperature and for 5 hours at 40° C. Then the mixture is neutralized with hydrochloric acid (1 M), partitioned between ethylacetate and brine. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→70:30) to give the title compound. LC (method 1): tR=1.04 min; Mass spectrum (ESI+): m/z=237 [M−H2O+H]+.

Workup

  1. custompartitioned between ethylacetate and brine
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→70:30)

Sources & evidence

ORD record
ord-219bb9445f344f0185bb8642bad999fa
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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