4-Bromo-3-fluoro-N-methoxy-N-methylbenzamide → (4-bromo-3-fluorophenyl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone

HRID 626175Notes

Reaction equation

HRID 626175 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][C:3]=1[F:14].[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[O:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1>O1CCCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([C:25]2[CH:26]=[CH:27][C:22]([O:21][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][O:15]3)=[CH:23][CH:24]=2)=[O:7])=[CH:4][C:3]=1[F:14]

Participants

4

Reactant 2

HCID 223138234-Bromo-3-fluoro-N-methoxy-N-methylbenzamideHCID 178419637HCID 178419637, compound

Product 1

HCID 89672898(4-bromo-3-fluorophenyl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanoneYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-3-fluoro-N-methoxy-N-methylbenzamide (1.00 g, 3.8 mmol) in dry tetrahydrofuran at 0° C. under nitrogen was added dropwise (4-(tetrahydro-2H-pyran-2-yloxy)phenyl)magnesium bromide (7.6 mmol). After addition, the reaction mixture was let warm to room temperature, stirred for 2 h., quenched with saturated ammonium chloride, and extracted with ethyl acetate. The extract was dried over sodium sulfate, concentrated, and purified by column chromatography to give the desired product as a colorless oil (1.10 g, 76% yield).

Workup

  1. additionAfter addition
  2. customquenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-012acaa372644a978f93ae547a9f95bc
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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