Diisopropylamine → 4-Bromo-N,N-diisopropylbenzamide

HRID 456850Notes

Reaction equation

HRID 456850 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH:11]([NH:14][CH:15]([CH3:17])[CH3:16])([CH3:13])[CH3:12]>ClCCl>[CH:11]([N:14]([CH:15]([CH3:17])[CH3:16])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=1)([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 36169884-Bromo-N,N-diisopropylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromobenzoyl chloride (10.0 g) in dry dichloromethane (60 mL) at 0° C. was slowly added diisopropylamine (19 mL; 3.0 eq). The reaction was stirred overnight under nitrogen and gradually warmed to room temperature. The solution was washed with two portions of water and the organics were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography eluting with 15% ethyl acetate. Near quantitative yield of product was obtained.

Workup

  1. customat 0° C.
  2. washThe solution was washed with two portions of water
  3. dry with materialthe organics were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 15% ethyl acetate

Sources & evidence

ORD record
ord-bb368a0f320b420aa2955bc3ddcc8cdb
Source dataset
uspto-grants-2007_03
Patent number
US07186733B2

Reaction notes

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