4-Toluenesulfonyl chloride → HCID 22274441, compound

HRID 494888Notes

Reaction equation

HRID 494888 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][CH2:11][OH:12])=[CH:7][C:6]=2[CH:13]=1.C(N(CC)CC)C.[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>C(Cl)Cl>[CH3:28][C:27]1[CH:29]=[CH:30][C:24]([S:21]([O:12][CH2:11][CH2:10][C:8]2[S:9][C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:13][C:6]=3[CH:7]=2)(=[O:23])=[O:22])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 222746535-Bromobenzo[b]thiophene-2-ethanol

Product 1

HCID 22274441HCID 22274441, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 165C (0.5 g) in methylene chloride (10 mL) was added triethylamine (0.3 g, 1.5 eq) followed by tosyl chloride (0.37 g, 1.0 ea). The solution was stirred at RT overnight and washed with 3×20 mL of water. The methylene chloride layer was concentrated to viscous oil (0.98 g, 68.1% potency, 83.5% yield). The crude product can be purified by crystallization from 20:80 EtOAc:hexane to give crystalline solid (0.48 g). 1H NMR (CDCl3, δ) 2.38 (s, 3H), 3.21 (t, 2H), 4.30 (t, 2H), 6.87 (s, 1H), 7.18 (d, 2H), 7.36 (d of d, 1H), 7.55 (d, 1H), 7.63 (d, 2H), 7.75 (d, 1H). MS (m/z): 428, 430 (M+NH4).

Workup

  1. washwashed with 3×20 mL of water
  2. concentrationThe methylene chloride layer was concentrated to viscous oil (0.98 g, 68.1% potency, 83.5% yield)
  3. customThe crude product can be purified by crystallization from 20:80 EtOAc

Sources & evidence

ORD record
ord-12c7cc75c4f743d7bdcfd9c5c6f7c8d0
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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