Water → Phosphorodichloridic acid, 3-(bromomethyl)phenyl ester

HRID 893585Notes

Reaction equation

HRID 893585 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[P:10](Cl)([Cl:13])([Cl:12])=[O:11].C(N(CC)CC)C.O>C(Cl)(Cl)(Cl)Cl>[P:10]([Cl:13])([Cl:12])(=[O:11])[O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][Br:1])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 137401503-(Bromomethyl)phenol

Product 1

HCID 14819637Phosphorodichloridic acid, 3-(bromomethyl)phenyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent3×

Procedure

To mixture of 17 g of m-bromomethylphenol in 150 ml of carbon tetrachloride under argon was added a solution of 25.5 g of phosphorous oxychloride in 25 ml of carbon tetrachloride. The solution was cooled in a water bath and a solution of 9.18 g of triethylamine in 35 ml of carbon tetrachloride was added dropwise with stirring over 40 minutes. This mixture was stirred in the water bath for 1 hour then overnight at room temperature, filtered through diatomaceous earth and washed with carbon tetrachloride. The mother liquor was taken to dryness giving 23-29 g of the desired compound as a pale yellow oil.

Workup

  1. temperatureThe solution was cooled in a water bath
  2. filtrationovernight at room temperature, filtered through diatomaceous earth
  3. washwashed with carbon tetrachloride

Sources & evidence

ORD record
ord-b45f5144359a42318ab6833260b977ac
Source dataset
uspto-grants-1992_06
Patent number
US05126291

Reaction notes

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