Water → 4-Fluoro-3-methoxymethoxybenzonitrile

HRID 1255618Notes

Reaction equation

HRID 1255618 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[OH:10].C(N(C(C)C)CC)(C)C.[CH3:20][O:21][CH2:22]Cl.O>ClCCl>[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH2:20][O:21][CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 207769814-Fluoro-3-hydroxybenzonitrile

Product 1

HCID 674399604-Fluoro-3-methoxymethoxybenzonitrileYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-3-hydroxybenzonitrile (25.0 g, 182 mmol), diisopropylethylamine (47.7 mL, 273 mmol) in dichloromethane (530 mL) was added chloromethyl methyl ether (16.6 mL, 219 mmol) dropwise at 0° C., and the mixture was stirred at room temperature overnight. Water was added, and the mixture was extracted with dichloromethane. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 4-fluoro-3-methoxymethoxybenzonitrile (33.0 g, quant.), which was used for the next step without purification.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2f232ce6d0664ccebece5ce3c1d1e6b5
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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