Chlorosulfonic acid → HCID 55279082, compound

HRID 2225107Notes

Reaction equation

HRID 2225107 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([Cl:15])(=[O:14])=[O:13])=[CH:4][CH:3]=1.ClS(O)(=O)=O.FC1C=CC=C2C=1CCCC2>ClCCl>[F:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([S:12]([Cl:15])(=[O:13])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24638Chlorosulfonic acidHCID 5790205-Fluoro-1,2,3,4-tetrahydronaphthaleneHCID 27746474-fluoronaphthalene-1-sulfonyl Chloride

Product 1

HCID 55279082HCID 55279082, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound was prepared according to Scheme 10 in a similar manner to the method for preparing 4-fluoro-naphthalene-1-sulfonyl chloride. Chlorosulfonic acid (2.65 g, 1.5 mL, 22.7 mmol) was stirred in a round-bottom flask cooled by a water bath at room temperature. 5-Fluoro-1,2,3,4-tetrahydro-naphthalene (0.62 g, 4.13 mmol) was added dropwise and the dark mixture was stirred for 30 minutes until gas evolution ceased. The reaction mixture was poured carefully over a mixture of ice (75 g) and dichloromethane (100 mL) and charged to a separatory funnel. The organic layer was separated, washed with brine and dried over MgSO4. Filtration and concentration in vacuo afforded a tan solid. Wt.: 860 mg (86%). 1H NMR (300 MHz, CDCl3) δ 7.97 (dd, 1H), 7.02 (t, 1H), 3.27 (m, 2H), 2.80 (m, 2H), 1.86 (m, 4H).

Workup

  1. customThe compound was prepared
  2. additioncharged to a separatory funnel
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationFiltration and concentration in vacuo
  7. customafforded a tan solid

Sources & evidence

ORD record
ord-9a2cb86fcfc049e9919d4e249f36aa3d
Source dataset
uspto-grants-2008_05
Patent number
US07378525B2

Reaction notes

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