Chlorosulfonic acid → 5-Bromo-2,3-dihydro-2-methyl-7-benzo[b]furanylsulfochloride

HRID 979734Notes

Reaction equation

HRID 979734 reaction equation
[Cl:1][S:2]([OH:5])(=[O:4])=[O:3].[Br:6][C:7]1[CH:16]=[CH:15][C:10]2[O:11][CH:12]([CH3:14])[CH2:13][C:9]=2[CH:8]=1>C(Cl)(Cl)Cl>[Br:6][C:7]1[CH:16]=[C:15]([O:3][S:2]([Cl:1])(=[O:5])=[O:4])[C:10]2[O:11][CH:12]([CH3:14])[CH2:13][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 133016015-Bromo-2-methyl-2,3-dihydro-1-benzofuran

Product 1

HCID 867411765-Bromo-2,3-dihydro-2-methyl-7-benzo[b]furanylsulfochlorideYield 65%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

470 g (4.03 moles) of chlorosulfonic acid are added dropwise over 20 minutes at -7° C. to a solution of 106 g (0.5 mole) of 5-bromo-2,3-dihydro-2-methylbenzo[b]furan in 300 ml of chloroform, and the mixture is then stirred for a further 15 minutes at 20°-25° C. The reaction mixture is taken up in ice/water, the organic phase is separated, and aqueous phase is extracted with two 500 ml portions of chloroform. The combined organic phases are washed with two 250 ml portions of water, dried over sodium sulfate, and concentrated, affording 101 g (65% of theory) of 5-bromo-2,3-dihydro-2-methyl-7-benzo[b]furanylsulfochloride.

Workup

  1. customthe organic phase is separated
  2. extractionaqueous phase is extracted with two 500 ml portions of chloroform
  3. washThe combined organic phases are washed with two 250 ml portions of water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4cb0146883cb465d958a1de54e18d073
Source dataset
uspto-grants-1987_01
Patent number
US04634465

Reaction notes

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