Dimethylformamide → HCID 66891080, compound

HRID 253281Notes

Reaction equation

HRID 253281 reaction equation
C1COCC1.[F:6][C:7]1[CH:8]=[C:9]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]([O:15][CH3:16])=[C:11]([CH2:13]O)[CH:12]=1.S(Cl)([Cl:27])=O.CN(C=O)C>C(OCC)(=O)C>[Cl:27][CH2:13][C:11]1[CH:12]=[C:7]([F:6])[CH:8]=[C:9]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 66890315{5-Fluoro-2-(methyloxy)-3-[(phenylmethyl)oxy]phenyl}methanol

Product 1

HCID 66891080HCID 66891080, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A THF (25 mL) solution of {5-fluoro-2-(methyloxy)-3-[(phenylmethyl)oxy]phenyl}methanol (6.94 g, 26 mmol) was cooled to 0° C. and was then treated with thionyl chloride (2.5 mL, 34 mmol) and DMF (5.0 mL, 65 mmol) for 30 min. Ethyl acetate and ice water were then added. The layers were partitioned, and the aqueous phase was extracted with ethyl acetate. The organic extracts were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo. The product, 1-(chloromethyl)-5-fluoro-2-(methyloxy)-3-[(phenylmethyl)oxy]benzene, was obtained as an orange oil (6.82 g, 24.3 mmol, 93% yield), which solidified upon storage in the freezer. 1H NMR (400 MHz, CDCl3): δ 7.45-7.26 (m, 5H), 6.72-6.66 (m, 2H), 5.09 (s, 2H), 4.61 (s, 2H), 3.91 (s, 3H).

Workup

  1. customThe layers were partitioned
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-647b36a0b77b4bd7ae0c574416c53b46
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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