2-Chloroanisole → 3-Chloro-4-methoxybenzene-1-sulfonyl chloride

HRID 1396050Notes

Reaction equation

HRID 1396050 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14]>>[Cl:6][C:7]1[CH:12]=[C:11]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:10]=[CH:9][C:8]=1[O:13][CH3:14]

Participants

3

Reactant 2

HCID 130112-ChloroanisoleHCID 24638Chlorosulfonic acid

Product 1

HCID 167674273-Chloro-4-methoxybenzene-1-sulfonyl chlorideYield 50%

Conditions

Temperature
55 °C

Procedure

Under N2 atmosphere, 41.25 mL chlorosulfonic acid was cooled in an ice bath, and under stirring 22.26 mL 2-chloroanisole was added dropwise. The mixture was heated to 55° C.; after 10 min. the heat source was removed and the mixture was stirred overnight at room temperature. The mixture was poured into ice water and extracted twice with DCM. The combined organic layers were dried over MgSO4 and evaporated to dryness. The residue was purified by flash chromatography (PA/EA 9:1) to give 24.94 g (50%) of a beige oil. 1H NMR (400 MHz, CDCl3) δ 4.03 (s, 3H), 7.08 (d, J=8.73 Hz, 1H), 7.94 (dd, J=9.03, 2.41 Hz, 1H), 8.06 (d, J=2.41 Hz, 1H).

Workup

  1. additionwas added dropwise
  2. customafter 10 min. the heat source was removed
  3. additionThe mixture was poured into ice water
  4. extractionextracted twice with DCM
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography (PA/EA 9:1)

Sources & evidence

ORD record
ord-a9a85b7fd0c242e6a13eff789c5f1163
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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