Phosphate → 4-(4-Bromophenoxy)benzene-1-sulfonyl chloride

HRID 1290698Notes

Reaction equation

HRID 1290698 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](C2C=CC=CC=2)=[CH:4][CH:3]=1.CC[O:16][CH2:17][CH3:18].[Cl:19][S:20]([OH:23])(=O)=[O:21].S(Cl)(Cl)(=O)=O.P([O-])([O-])([O-])=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][C:17]2[CH:18]=[CH:4][C:3]([S:20]([Cl:19])(=[O:23])=[O:21])=[CH:2][CH:7]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1061PhosphateHCID 24638Chlorosulfonic acidHCID 24648Sulfuryl chlorideHCID 69416353HCID 69416353, compound

Product 1

HCID 122497414-(4-Bromophenoxy)benzene-1-sulfonyl chlorideYield 159.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 12.45 g (50 mmol) of 4-bromobiphenyl ether in 50 mL of dichloromethane at -5° C. was added 9.9 mL (17.4 g, 150 mmol) of chlorosulfonic acid dropwise. After the addition was complete, the reaction was allowed to warm to room temperature for one hour (needed to completely convert the initially formed sulfonic acid to the sulfonyl chloride). The reaction mixture was added to cold pH 7 phosphate buffer (ca. 0.5M) and twice extracted with 50 mL of dichloromethane. The organic extracts were combined and washed with brine, dried over sodium sulfate, and concentrated. Addition of hexane to the residual syrup and re-concentration gave 13.9 g (80%) of 4-(4-bromophenoxy)benzenesulfonyl chloride as a white powder: mp 80.9° C.

Workup

  1. additionAfter the addition
  2. extractiontwice extracted with 50 mL of dichloromethane
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. additionAddition of hexane
  7. concentrationto the residual syrup and re-concentration

Sources & evidence

ORD record
ord-680cb9d273d6457abebe78ba0c2e8453
Source dataset
uspto-grants-1998_05
Patent number
US05753653

Reaction notes

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