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Ammonium Chloride → (5-Bromo-2,4-difluoro-phenyl)-(3-fluoro-phenyl)-methanol

HRID 503162
Notes
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Reaction equation

HRID 503162 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[C:5]([F:9])=[CH:4][C:3]=1[F:10].C([Li])CCC.[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21].[Cl-].[NH4+]>C(OCC)C.CCCCCC>[Br:8][C:6]1[C:5]([F:9])=[CH:4][C:3]([F:10])=[C:2]([CH:20]([C:19]2[CH:22]=[CH:23][CH:24]=[C:17]([F:16])[CH:18]=2)[OH:21])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 680093-FluorobenzaldehydeHCID 105645111,5-Dibromo-2,4-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 22260768(5-Bromo-2,4-difluoro-phenyl)-(3-fluoro-phenyl)-methanol

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

A total of 2.02 g of 1,5-dibromo-2,4-difluorobenzene obtained in Production Example II-5-a was dissolved in 38 ml of diethyl ether, and 4.9 ml of a 1.58 M solution of n-butyllithium in hexane was added under stirring at −70° C. After stirring for 1 hour, 4.9 ml of m-fluorobenzaldehyde was added and the mixture was stirred for 15 minutes. Saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extracting with ethyl acetate. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:10), to give 0.96 g of the title compound.

Workup

  1. stirringAfter stirring for 1 hour
  2. stirringthe mixture was stirred for 15 minutes
  3. extractionby extracting with ethyl acetate
  4. washThe resulting organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified
  8. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:10)

Sources & evidence

ORD record
ord-94206b409d9c4e3b89aa1e6ca590e3d1
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07776890B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes