4-(Trifluoromethoxy)benzoyl Chloride → HCID 21930291, compound

HRID 1243653Notes

Reaction equation

HRID 1243653 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1.[I:15][C:16]1[CH:22]=[C:21]([Br:23])[CH:20]=[CH:19][C:17]=1[NH2:18]>N1C=CC=CC=1>[Br:23][C:21]1[CH:20]=[CH:19][C:17]([NH:18][C:8](=[O:9])[C:7]2[CH:11]=[CH:12][C:4]([O:3][C:2]([F:14])([F:13])[F:1])=[CH:5][CH:6]=2)=[C:16]([I:15])[CH:22]=1

Participants

4

Reactant 2

HCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 8239344-Bromo-2-iodoaniline

Product 1

HCID 21930291HCID 21930291, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled 30 mL vial containing a stirring bar and 4-trifluoromethoxybenzoylchloride (0.70 g, 3.12 mmol), 2-iodo-4-bromoaniline (0.837 g, 2.81 mmol) in 3 mL of anhydrous pyridine was added. The bath was then removed. The reaction solution was stirred at room temperature overnight and 50 mL of EtOAc was added. The resulting solution was poured into 100 mL of 10% aq. HCl. The layers were stirred and then the organic layer was separated and washed with water (2×50 mL), dried with Na2SO4 and concentrated, revealing the desired product. 1H-NMR (400 MHz, CDCl3): δ=7.37 (d, 8.4 Hz, 2HCF3OCCH), 7.53 (m, 1H, ICNCCH), 7.96 (d, 1.6 Hz, 1H, BrCCHCI), 8.8 (d, 8.8 Hz, 2H, CHCHCCOCF3), 8.21 (s, 1H, NH), 8.34 (d, 8.8 Hz, 1H, ICNCCHCH). MS (electrospray) 486 (MH+), 488 (MH++2).

Workup

  1. additionTo a cooled 30 mL vial containing a stirring bar
  2. customThe bath was then removed
  3. addition50 mL of EtOAc was added
  4. additionThe resulting solution was poured into 100 mL of 10% aq. HCl
  5. stirringThe layers were stirred
  6. customthe organic layer was separated
  7. washwashed with water (2×50 mL)
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-dc4b80aeb1e3449b908a26aad6b7f52c
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Reaction notes

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