Hydrochloric Acid → 4-Bromo-N,N-diisopropylbenzamide

HRID 2192959Notes

Reaction equation

HRID 2192959 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:18]([NH:21][CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19].Cl>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:21]([CH:22]([CH3:24])[CH3:23])[CH:18]([CH3:20])[CH3:19])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 8471TriethylamineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 36169884-Bromo-N,N-diisopropylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution 4-bromobenzoyl chloride (25 g, 114 mmoles) in THF at 0° C. (200 mL) was added triethylamine (63.5 Ml, 456 mmoles) dropwise followed by diisopropylamine (32.5 mL, 228 mmol). The solution was allowed to stir overnight. The next day the reaction mixture was acidified with 1 N HCl and extracted with CH2Cl2. The organic layer was basified with sat. NaHCO3 wash and dried with MgSO4, filtered, and concentrated. Column chromatography on silica gel 100% Hex. to 100% EtOAc provided the desired product as a yellow solid. 1H NMR (600 MHz, CD3OD) δ 7.60 (d, 2H), 7.23 (d, 2H), 3.30 (br s, 1H), 3.29 (br s, 1H), 1.5, (br s, 6H), 1.22 (br s, 6H). LRMS (ESI) calc'd for (C13H19BrNO) [M+H]+, 284.1; found 284.1.

Workup

  1. extractionextracted with CH2Cl2
  2. washwash
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-98dd9fd6f2d2490cb66cea50b7e46f48
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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