Sulfuryl chloride → (Chloro(phenylmethoxy)phosphoryl)oxymethylbenzene

HRID 232027Notes

Reaction equation

HRID 232027 reaction equation
S(Cl)([Cl:4])(=O)=O.[P:6]([O-:23])([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[P:6]([Cl:4])([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:23]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 21904359Dibenzylphosphite

Product 1

HCID 4641201(Chloro(phenylmethoxy)phosphoryl)oxymethylbenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of sulphuryl chloride (3.48 g) in toluene (25 ml) was added to a stirred solution of dibenzyl phosphite (6.08 ml) in toluene (75 ml) under nitrogen. The mixture was stirred for 75 min. under nitrogen, washed with 8% sodium bicarbonate solution (75 ml) and the organic layer separated and dried over anhydrous sodium sulphate. After filtration the filtrate was evaporated and dried to give dibenzyl chlorophosphate (7.75 g) as a colourless oil. Potassium carbonate (1.81 g) was added to a solution of 5-hydroxy-1,4-naphthalenedione (2.18 g) in acetonitrile (300 ml) with stirring at room temperature. Freshly prepared dibenzyl chlorophosphate (7.75 g, see above) in acetonitrile (50 ml) was added and the mixture stirred for 20 h. Potassium carbonate (907 mg) was then added and a further quantity (907 mg) of potassium carbonate added after another 24 h. The mixture was evaporated to dryness and dried in vacuo to give an oil. The oil was subjected to column chromatography (silica, 500 g, 70-230 mesh) eluting with dichloromethane:acetone (96:4). Fractions (250 ml) were collected and fractions 4-12 combined and the solvent evaporated. After drying in vacuo the title compound (3.18 g) was obtained as an orange solid; δ(CDCl3) 5.28 (OCH2), 7.38 (Ph).

Workup

  1. washwashed with 8% sodium bicarbonate solution (75 ml)
  2. customthe organic layer separated
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationAfter filtration the filtrate
  5. customwas evaporated
  6. customdried

Sources & evidence

ORD record
ord-c1c12659b8f74783a402e2b32c0ad828
Source dataset
uspto-grants-1989_07
Patent number
US04851399

Reaction notes

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