p-Toluenesulfonic acid → 1-(4-Bromo-3-fluorophenyl)-2,2-diethoxyethanone

HRID 452026Notes

Reaction equation

HRID 452026 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([OH:11])[OH:10])=[CH:4][C:3]=1[F:13].F[C:15]1C=C(C2C=NC3N(C(CC4C=C5C(=CC=4)N=CC=C5)=CN=3)N=2)C=C[C:16]=1C(NC[C@H](O)C)=O.C([O-])([O-])O[CH2:50][CH3:51].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([O:10][CH2:50][CH3:51])[O:11][CH2:15][CH3:16])=[CH:4][C:3]=1[F:13]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 533743182-fluoro-N-[(2R)-2-hydroxypropyl]-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide2×HCID 53630039EthylorthoformateHCID 575165211-(4-Bromo-3-fluorophenyl)-2,2-dihydroxyethanone

Product 1

HCID 575165221-(4-Bromo-3-fluorophenyl)-2,2-diethoxyethanone

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-(4-bromo-3-fluorophenyl)-2,2-dihydroxyethanone and 4-bromo-3-fluorophenyl)(oxo)acetaldehyde (crude product from Step 3, 7.0 g, 28 mmol) in toluene (50 mL) was added ethyl orthoformate (12 mL, 70 mmol) and p-toluenesulfonic acid (200 mg, 1 mmol). The reaction mixture was refluxed for 4 h. The reaction mixture was cooled to RT, diluted with ethyl acetate, washed with aqueous sodium bicarbonate, water, brine, and dried over magnesium sulfate. Concentration under reduced pressure gave the desired product which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. washwashed with aqueous sodium bicarbonate, water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-099f00c91bb941e4ab42dba41f944f2c
Source dataset
uspto-grants-2013_07
Patent number
US08487096B2

Reaction notes

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