Sodium Carbonate → HCID 72211834, compound

HRID 2368916Notes

Reaction equation

HRID 2368916 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10]O)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:13].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[Cl:13][CH2:10][C:4]1[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24819Phosphorus pentachlorideHCID 26985456(3-Fluoro-5-methoxyphenyl)methanol

Product 1

HCID 72211834HCID 72211834, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of (3-fluoro-5-methoxyphenyl)methanol (4.9 g, 30 mmol) in CCl4 (50 mL), PCl5 (13 g, 60 mmol) was added. The mixture was stirred at room temperature for 1 h. To this mixture, saturated Na2CO3 solution was slowly added until pH was adjusted to 7˜8. The mixture was extracted with DCM (3×15 mL), and the organic phase was concentrated to give a colorless oil, which was purified by silica-gel column chromatography (100% petroleum ether) to give 2.9 g of 1-(chloromethyl)-3-fluoro-5-methoxybenzene. 1H NMR (CDCl3): δ 6.68-6.72 (m, 2H), 6.54-6.59 (m, 1H), 4.51 (s, 2H), 3.81 (s, 3H).

Workup

  1. extractionThe mixture was extracted with DCM (3×15 mL)
  2. concentrationthe organic phase was concentrated
  3. customto give a colorless oil, which
  4. customwas purified by silica-gel column chromatography (100% petroleum ether)

Sources & evidence

ORD record
ord-cf7a3d9586c14bc4ae748cb8b3557560
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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