Hydrochloric Acid → HCID 3738693, compound

HRID 588668Notes

Reaction equation

HRID 588668 reaction equation
[Br:1]Br.[CH3:3][C:4]12[CH2:14][CH:8]3[CH2:9][C:10]([CH3:13])([CH2:12][C:6]([C:15]([OH:17])=[O:16])([CH2:7]3)[CH2:5]1)[CH2:11]2.Cl.[O-]S([O-])=O.[Na+].[Na+]>[Fe].C(OCC)(=O)C>[Br:1][C:8]12[CH2:7][C:6]3([C:15]([OH:17])=[O:16])[CH2:12][C:10]([CH3:13])([CH2:11][C:4]([CH3:3])([CH2:5]3)[CH2:14]1)[CH2:9]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 24437Sodium SulfiteHCID 27362243,5-Dimethyladamantane-1-carboxylic acid

Product 1

HCID 3738693HCID 3738693, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 mL round-bottomed flask, bromine (3 mL) was cooled to 0° C. and iron (0.56 g) was added. The mixture was stirred at 0° C. for 30 minutes. 3,5-dimethyladamantane-1-carboxylic acid (0.5 g) was added. The mixture was stirred at room temperature overnight. After adding ice and 6N aqueous HCl (10 mL), ethyl acetate (20 mL), and saturated aqueous Na2SO3 were added. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with saturated Na2SO3 (50 mL, 3×) and dried over Na2SO4. After filtration and removal of the solvent, the product was used directly in the next step.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. additionwere added
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with saturated Na2SO3 (50 mL, 3×)
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and removal of the solvent

Sources & evidence

ORD record
ord-d72a206201c44d4592f45325b65f34ce
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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