Benzene, 1-bromo-4-(trifluoromethyl)- → HCID 22496021, compound

HRID 1815989Notes

Reaction equation

HRID 1815989 reaction equation
[Li]C(CC)C.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.CON(C)[C:20](=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1>C1COCC1>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][C:20]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[O:30])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 22496069N-Methoxy-2-(4-methoxyphenyl)-N-methylacetamideHCID 178418400CID 53628100

Product 1

HCID 22496021HCID 22496021, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of sec-BuLi (1.3 M in THF, 22.6 mL, 29.5 mmole) in dry THF (50 mL) was added 4-bromobenzotrifluoride (3.3 g, 14.7 mmole) in dry THF (20 mL) dropwise at −78° C. After 20 min, N-methoxy-N-methyl-2(4-methoxyphenyl)acetamide (1.5 g, 7.4 mmole) in dry THF (20 mL) was added dropwise. After 1 hr the mixture was quenched with saturated NH4Cl (10 mL), warmed to RT, and extracted with Et2O (3×20 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was chromatographed on silica gel (15% EtOAc/hexanes) to give the title compound (2.2 g, 100%) as a slightly-yellow solid: TLC (1.5% EtOAc/hexanes) Rf0.81; 1H NMR (300 MHz, CDCl3) δ 8.10 (d, J=8.2 Hz, 2 H), 7.72 (d, J=8.2 Hz, 2 H), 7.18 (d, J=8.7 Hz, 2 H), 6.88 (d, J=8.7 Hz, 2 H), 4.25 (s, 2 H), 3.79 (s, 3 H).

Workup

  1. customAfter 1 hr the mixture was quenched with saturated NH4Cl (10 mL)
  2. extractionextracted with Et2O (3×20 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0dbace3cc9774bc18831c4b3afc7b830
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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