Chlorosulfonic acid → (E)-ethyl 3-(4-(4-(chlorosulfonyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate

HRID 45690Notes

Reaction equation

HRID 45690 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:16]=[C:17](\[CH3:23])/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:5]=[C:6]([F:15])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl:24][S:25](O)(=[O:27])=[O:26]>C(Cl)Cl>[Cl:24][S:25]([C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[C:2]([F:1])=[CH:3][C:4](/[CH:16]=[C:17](\[CH3:23])/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5][C:6]=2[F:15])=[CH:10][CH:11]=1)(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acid2×HCID 70876774(E)-ethyl 3-(3,5-difluoro-4-phenoxyphenyl)-2-methylacrylate2×

Product 1

HCID 86672338(E)-ethyl 3-(4-(4-(chlorosulfonyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-ethyl 3-(3,5-difluoro-4-phenoxyphenyl)-2-methylacrylate (intermediate 41.2) (1 g, 3.14 mmol) in DCM (3.14 mL) under N2 was added chlorosulfonic acid (0.419 mL, 6.28 mmol) dropwise. After 1 hour an additional 0.209 mL chlorosulfonic acid was added. After an additional hour the reaction mixture was quenched with ice-water and extracted into EtOAc (2×200 mL). The combined organic layers were dried briefly (<10 min) over Na2SO4 and concentrated to recover 1.283 g of the title compound (98%) as a yellow oil.

Workup

  1. customAfter an additional hour the reaction mixture was quenched with ice-water
  2. extractionextracted into EtOAc (2×200 mL)
  3. dry with materialThe combined organic layers were dried briefly (<10 min) over Na2SO4
  4. concentrationconcentrated
  5. customto recover 1.283 g of the title compound (98%) as a yellow oil

Sources & evidence

ORD record
ord-9cbe71f484454d9cbec97969b8f7d00e
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Reaction notes

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