Dichloromethane → 7-(Dimethoxythiophosphorylmethyl) naphthalene-1-carboxylic acid tert-butyl ester

HRID 496326Notes

Reaction equation

HRID 496326 reaction equation
[P:1]([O-:6])([O:4][CH3:5])[S:2]C.[C:7]([O:11][C:12]([C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH2:24]Br)[CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[OH-].[Na+].Cl[CH2:29]Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[C:7]([O:11][C:12]([C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][P:1]([O:6][CH3:29])([O:4][CH3:5])=[S:2])[CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 121243517-Bromomethylnaphthalene-1-carboxylic acid tert-butyl esterHCID 86596782Dimethyl thiophosphite

Product 1

HCID 697362767-(Dimethoxythiophosphorylmethyl) naphthalene-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A solution of dimethyl thiophosphite (3.84 g, 30.5 mmol), crude 7-bromomethylnaphthalene-1-carboxylic acid tert-butyl ester (11.2 g, 34.9 mmol) and triethylbenzylammonium chloride (0.72 g, 3.17 mmol) in dichloromethane (100 mL) was cooled on an ice bath and a solution of sodium hydroxide (12.7 g, 0.317 mol) in water (12.7 mL) was added slowly with vigorous stirring. The ice bath was then removed and the mixture stirred overnight. The next morning, it was washed with water, dried (magnesium sulfate), and the solvent removed under reduced pressure to give crude 7-(dimethoxythiophosphorylmethyl) naphthalene-1-carboxylic acid tert-butyl ester (See FIG. 1) (10.38 g) as orange oil.

Workup

  1. customThe ice bath was then removed
  2. washThe next morning, it was washed with water
  3. dry with materialdried (magnesium sulfate)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a1335bbf37fd4126b76753cf24cfda59
Source dataset
uspto-grants-2005_09
Patent number
US06943267B1

Reaction notes

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