N-bromobutanimide → HCID 19841452, compound

HRID 1638748Notes

Reaction equation

HRID 1638748 reaction equation
[Br:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[C:11]([Cl:12])=[CH:10][C:8]([NH2:9])=[CH:7][C:6]=1[Cl:13].[Br:19]N1C(=O)CCC1=O>C1C=CC=CC=1>[Br:19][C:10]1[C:11]([Cl:12])=[C:5]([O:4][C:3]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:2]=2[Br:1])[C:6]([Cl:13])=[CH:7][C:8]=1[NH2:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 19841464HCID 19841464, compound

Product 1

HCID 19841452HCID 19841452, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into a magnetically stirred solution of 4-(2-bromo-4-chlorophenoxy)-3,5-dichloroaniline (6.38 grams, 17.36 mmol) in benzene (35 milliliters) was added N-bromosuccinimide (3.71 grams, 20.83 mmol). The reaction mixture was stirred for two hours at room temperature, transferred to a separatory funnel and washed with saturated Na2SO3 solution (2x), water (2x) and brine (1x). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude product which when subjected to flash column chromatography on 760 grams of silica gel (4:1 hexane:ethyl acetate) afforded pure 2-bromo-4-(2-bromo-4-chlorophenoxy)-3,5-dichloroaniline (5.15 grams, 11.53 mmol, 66%). Elemental analysis of the product indicated the following:

Workup

  1. customtransferred to a separatory funnel
  2. washwashed with saturated Na2SO3 solution (2x), water (2x) and brine (1x)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product which when

Sources & evidence

ORD record
ord-e63ab20f44984e6aaad0532c77aca281
Source dataset
uspto-grants-1989_11
Patent number
US04880838

Reaction notes

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