Dichloromethane → HCID 13037524, compound

HRID 2058923Notes

Reaction equation

HRID 2058923 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([P:8]2(=[O:23])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:10][N:9]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.C(Cl)Cl.[Br:27]Br>C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([P:8]2(=[O:23])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:10][N:9]2[C:17]2[CH:18]=[CH:19][C:20]([Br:27])=[CH:21][CH:22]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 24408BromineHCID 13037506HCID 13037506, compound

Product 1

HCID 13037524HCID 13037524, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-2-phenyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (1.0 g, 0.003 mol) in 25 ml. of methylene chloride was added dropwise a solution of bromine (0.8 g, 0.1 mol) in 25 ml. of methylene chloride with constant stirring. The reaction mixture was stirred for one hour and washed with water, then sodium bisulfite, again with water, dried over magnesium sulfate and concentrated in vacuo to yield a yellow solid. The yellow solid was slurried in anhydrous diethyl ether to yield 1-(4-fluorophenyl)-2-(4-bromophenyl)-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (0.7 g, 56.4% yield) as a white solid having a melting point of 201°-205° C. and the following analysis:

Workup

  1. washwashed with water
  2. dry with materialsodium bisulfite, again with water, dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto yield a yellow solid

Sources & evidence

ORD record
ord-13637d6bfef34dca93174de3d70636be
Source dataset
uspto-grants-1982_03
Patent number
US04319913

Reaction notes

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