4-Fluorobenzoyl chloride → HCID 53909840, compound

HRID 2412946Notes

Reaction equation

HRID 2412946 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([CH3:12])[CH2:10][NH2:11])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>O>[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:11][CH2:10][C:9]([CH3:12])=[CH:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 54435506HCID 54435506, compound

Product 1

HCID 53909840HCID 53909840, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a vigorously stirred mixture of 19.8 g (0.12 mole) of 3-(4-fluorophenyl)-2-methyl-2-propen-1-amine and 30.2 g (0.36 mole) of sodium bicarbonate in 500 ml water at 5° C. was added dropwise 22.2 g (0.14 mole) of 4-fluorobenzoyl chloride. The mixture was stirred another 3 hours at 5° C. then at room temperature overnight. The white solid which had formed was collected, washed with saturated sodium bicarbonate solution, then with water, then with hexane, then air dried to give 33.4 g (97%) of product, m.p. 107°-109° C.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe white solid which had formed
  4. customwas collected
  5. washwashed with saturated sodium bicarbonate solution
  6. dry with materialwith water, then with hexane, then air dried

Sources & evidence

ORD record
ord-80c8dbf38b7f4fb3a64325166d1c677c
Source dataset
uspto-grants-1985_01
Patent number
US04495196

Reaction notes

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