Water → HCID 86703533, compound

HRID 1849667Notes

Reaction equation

HRID 1849667 reaction equation
[F:1][C:2]1([F:14])[CH:9]2[CH2:10][C:5]3([CH2:12][OH:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[Cl:15][C:16]1[C:17](F)=[CH:18][C:19]([F:29])=[C:20]([CH:28]=1)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[Cl:15][C:16]1[C:17]([O:13][CH2:12][C:5]23[CH2:10][CH:9]4[CH2:8][CH:7]([CH2:11][CH:3]([C:2]4([F:14])[F:1])[CH2:4]2)[CH2:6]3)=[CH:18][C:19]([F:29])=[C:20]([CH:28]=1)[C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 58042499tert-butyl 5-chloro-2,4-difluorobenzoateHCID 66521760(4,4-Difluorotricyclo[3.3.1.1~3,7~]decan-1-yl)methanol

Product 1

HCID 86703533HCID 86703533, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (4,4-difluoroadamantan-1-yl)methanol (1.00 g, 4.90 mmol) and tert-butyl 5-chloro-2,4-difluorobenzoate (1.84 g, 7.40 mmol) in anhydrous dimethylsulfoxide (20 mL) was added cesium carbonate (3.22 g, 9.90 mmol). The mixture was stirred at 70° C. for 16 hours. The mixture was then cooled to ambient temperature, and mixed with water (50 mL). The white solid was filtered and washed with hexanes and dried by air give the title compound as colorless solid (1.70 g, 80%): MS (ES+) m/z 431.1, 433.1 (M+1); 375.0, 377.0 (M−55).

Workup

  1. temperatureThe mixture was then cooled to ambient temperature
  2. filtrationThe white solid was filtered
  3. washwashed with hexanes
  4. customdried by air

Sources & evidence

ORD record
ord-b45bb87bb97d4f58a568d4826b3cfea3
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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