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Ammonium Chloride → (5-Bromo-2-fluorophenyl)(6-chloro-2-fluoro-3-(methoxymethoxy)pyridin-4-yl)methanol

HRID 335899
Notes
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Reaction equation

HRID 335899 reaction equation
C([Li])CCC.[Cl:6][C:7]1[N:12]=[C:11]([F:13])[C:10]([O:14][CH2:15][O:16][CH3:17])=[CH:9][CH:8]=1.[Br:18][C:19]1[CH:20]=[CH:21][C:22]([F:27])=[C:23]([CH:26]=1)[CH:24]=[O:25].[Cl-].[NH4+]>C1COCC1.CCOC(C)=O.O>[Br:18][C:19]1[CH:20]=[CH:21][C:22]([F:27])=[C:23]([CH:24]([C:9]2[CH:8]=[C:7]([Cl:6])[N:12]=[C:11]([F:13])[C:10]=2[O:14][CH2:15][O:16][CH3:17])[OH:25])[CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 574756416-Chloro-2-fluoro-3-(methoxymethoxy)pyridineHCID 178418339Butyllithium

Product 1

HCID 86658355(5-Bromo-2-fluorophenyl)(6-chloro-2-fluoro-3-(methoxymethoxy)pyridin-4-yl)methanol

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent3×
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

DIPA (0.750 mL, 5.35 mmol) was dissolved in dry THF (20 mL) under nitrogen and cooled in a dry ice bath to −78° C. Butyllithium solution (2.5 M in hexanes, 2.0 mL, 5.00 mmol) was added and the solution was stirred for a few minutes. A solution of 6-chloro-2-fluoro-3-(methoxymethoxy)pyridine (0.864 g, 4.51 mmol) in dry THF (10 mL) was added slowly and the resulting solution stirred for 40 minutes. A solution of 5-bromo-2-fluorobenzaldehyde (1.02 g, 5.05 mmol) in dry THF (1 mL) was added dropwise. After 10 minutes saturated ammonium chloride (10 mL), water (100 mL) and EtOAc (100 mL) were added and the phases mixed and separated. The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to EtOAc gradient) gave the desired (5-bromo-2-fluorophenyl)(6-chloro-2-fluoro-3-(methoxymethoxy)pyridin-4-yl)methanol.

Workup

  1. stirringthe resulting solution stirred for 40 minutes
  2. additionthe phases mixed
  3. customseparated
  4. dry with materialThe organic was dried with magnesium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customPurification

Sources & evidence

ORD record
ord-90437431dd774604ad2ea55e7c819041
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883782B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes