Pyridine → HCID 66891035, compound

HRID 253272Notes

Reaction equation

HRID 253272 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:18]O)[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]=1[O:8][CH3:9].N1C=CC=CC=1.S(Cl)([Cl:28])=O>ClCCl>[Cl:28][CH2:18][C:4]1[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 24386Thionyl ChlorideHCID 66890573HCID 66890573, compound

Product 1

HCID 66891035HCID 66891035, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {3-fluoro-4-(methyloxy)-5-[(phenylmethyl)oxy]phenyl}methanol (2.69 g, 10.26 mmol.) in dichloromethane (40 mL) was cooled to 0° C. followed by addition of pyridine (913 uL, 11.3 mmol.) then thionyl chloride (750 uL, 10.3 mmol.). The mixture was then allowed to warm to room temperature followed by addition of a second aliquot of pyridine (400 uL). After 5 minutes the organic solution was washed once with 0.1M aqueous hydrochloric acid then dried over anhydrous magnesium sulfate. Filtration and concentration afforded 5-(chloromethyl)-1-fluoro-2-(methyloxy)-3-[(phenylmethyl)oxy]benzene (2.88 g, 100% yield) as a clear oil that was used without further purification. GCMS for C15H14O2FCl: 280 (M+).

Workup

  1. washAfter 5 minutes the organic solution was washed once with 0.1M aqueous hydrochloric acid
  2. dry with materialthen dried over anhydrous magnesium sulfate
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-6b28564e19644e5ca1b2d0e5f1f5353d
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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