Bromine → N-[2-(4-Bromo-phenyl)-1,1-dimethyl-ethyl]-formamide

HRID 76149Notes

Reaction equation

HRID 76149 reaction equation
[CH3:1][C:2]([NH:11][CH:12]=[O:13])([CH3:10])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Br:18]Br>C(Cl)Cl>[Br:18][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][C:2]([NH:11][CH:12]=[O:13])([CH3:1])[CH3:10])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 104077N-(1,1-Dimethyl-2-phenylethyl)formamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 88861428N-[2-(4-Bromo-phenyl)-1,1-dimethyl-ethyl]-formamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

1.00 g (5.64 mmol) N-(1,1-dimethyl-2-phenyl-ethyl)-formamide (I34) is added to 8 mL DCM and cooled down to −5° C. Then 1.50 g (11.3 mmol) aluminium chloride is added by several portions, stirred for 5 min, before 0.9 g (5.64) bromine is added over a period of 1 min. Having finished the addition, the mixture is stirred for two more minutes at 0° C., poured onto ice water and extracted with DCM. The organic layer is dried with MgSO4 and the solvent is removed in vacuo.

Workup

  1. additionis added over a period of 1 min
  2. additionthe addition
  3. additionpoured onto ice water
  4. extractionextracted with DCM
  5. dry with materialThe organic layer is dried with MgSO4
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-e60c9785d9d342bab0b15d0c0b8c3978
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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