Hydrochloric Acid → HCID 86703527, compound

HRID 1849662Notes

Reaction equation

HRID 1849662 reaction equation
[Cl:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[OH:12])[CH2:3]1)[CH2:9]2.CC(C)([O-])C.[K+].[Cl:19][C:20]1[C:21](F)=[CH:22][C:23]([F:29])=[C:24]([CH:28]=1)[C:25]([OH:27])=[O:26].Cl>CS(C)=O.O>[Cl:19][C:20]1[C:21]([O:12][CH:5]2[CH:4]3[CH2:10][CH:8]4[CH2:9][C:2]([Cl:1])([CH2:11][CH:6]2[CH2:7]4)[CH2:3]3)=[CH:22][C:23]([F:29])=[C:24]([CH:28]=1)[C:25]([OH:27])=[O:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12660028HCID 12660028, compoundHCID 148764175-Chloro-2,4-difluorobenzoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 86703527HCID 86703527, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 5-chloroadamantan-2-ol (2.00 g, 10.70 mmol) in anhydrous dimethylsulfoxide (50 ml) was added potassium tert-butoxide (3.01 g, 26.80 mmol) and the reaction mixture was stirred at ambient temperature for 30 minutes. 5-chloro-2,4-difluorobenzoic acid (2.06 g, 10.70 mmol) was added to the reaction mixture, stirring was continued for 2 hours. The reaction mixture was acidified to pH=1 with 5% aqueous hydrochloric acid solution and diluted with water (100 mL), the white precipitate was filtered, washed with water and dried to afforded the title compound as colorless solid (3.30 g, 86%), containing o-substituted regioisomer, which was used for next step without further purification: MS (ES+) m/z 359.2, 361.2 (M+1), MS (ES−) m/z 357.1, 359.1 (M−1).

Workup

  1. stirringstirring
  2. waitwas continued for 2 hours
  3. filtrationthe white precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-632ad81af0224396a6a0ecd5c5046bdf
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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