1-Bromo-4-fluorobenzene → HCID 3055543, compound

HRID 1447653Notes

Reaction equation

HRID 1447653 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.[Br:18][C:19]1[CH:24]=[CH:23][C:22](F)=[CH:21][CH:20]=1>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:22]2[CH:23]=[CH:24][C:19]([Br:18])=[CH:20][CH:21]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 99931-Bromo-4-fluorobenzeneHCID 24758Sodium hydrideHCID 86736721HCID 86736721, compound

Product 1

HCID 3055543HCID 3055543, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 8 ml of dimethylsulfoxide and 0.820 g of sodium hydride as a 50% oil dispersion was heated at 50° C. for 45 minutes and was then cooled to 20° C. 3 g of cis 7-dimethylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol were added thereto and the mixture stood at room temperature for 15 minutes after which 2 ml of p-bromo-fluorobenzene were added thereto. The mixture was heated at 90°±5° C. for one hour and was then cooled to 20° C. and extracted with methylene chloride. The organic phase was washed with water, dried and evaporated to dryness to obtain 6 g of cis N,N-dimethyl-5-[4-bromophenoxy]-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-amine in the form of a yellow oil.

Workup

  1. temperaturewas then cooled to 20° C
  2. temperatureThe mixture was heated at 90°±5° C. for one hour
  3. temperaturewas then cooled to 20° C.
  4. extractionextracted with methylene chloride
  5. washThe organic phase was washed with water
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-448d73bc15b3442083c39ef87c463d23
Source dataset
uspto-grants-1979_12
Patent number
US04177292

Reaction notes

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