1-Chloro-2-fluorobenzene → HCID 86736722, compound

HRID 1447658Notes

Reaction equation

HRID 1447658 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:17])[C@@H:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[C@H:7]([OH:16])[CH2:6]1.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1F>CS(C)=O>[CH3:3][N:4]([CH3:17])[C@@H:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[C@H:7]([O:16][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[Cl:18])[CH2:6]1

Participants

5

Reactant 3

HCID 95831-Chloro-2-fluorobenzeneHCID 24758Sodium hydrideHCID 86736721HCID 86736721, compound

Product 1

HCID 86736722HCID 86736722, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

0.6 ml of dimethylsulfoxide were added to 65 mg of sodium hydride in the form of a 50% oil dispersion and the mixture was held at 25° C. for 30 minutes and was then heated to 60° C. and then cooled to 25° C. 205 mg of cis 7-dimethylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol were added thereto and after standing at room temperature for 15 minutes, 0.15 ml of o-chlorofluorobenzene was added thereto. The mixture was heated at 80° C. for 30 minutes and then was cooled to 20° C. and extracted with methylene chloride. The organic phase was washed with water, dried and evaporated to dryness to obtain 370 mg of cis N,N-dimethyl-5-[2-chlorophenoxy]-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-amine in the form of an orange oil.

Workup

  1. temperaturecooled to 25° C
  2. waitafter standing at room temperature for 15 minutes
  3. temperatureThe mixture was heated at 80° C. for 30 minutes
  4. temperaturewas cooled to 20° C.
  5. extractionextracted with methylene chloride
  6. washThe organic phase was washed with water
  7. customdried
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-ee0f58d91c044c34b549c1c8de12824f
Source dataset
uspto-grants-1979_12
Patent number
US04177292

Reaction notes

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