4-Bromoaniline → HCID 91559901, compound

HRID 1485639Notes

Reaction equation

HRID 1485639 reaction equation
ClOC(C)(C)C.[CH2:7]1[S:10][CH2:9][CH2:8]1.[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.CCCCCCC=CCCC>ClCCl>[Br:11][C:12]1[CH:18]=[CH:17][C:15]([N:16]2[CH2:9][CH2:8][CH2:7][S:10]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 78074-BromoanilineHCID 9251ThietaneHCID 136496Undec-4-eneHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 91559901HCID 91559901, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-15 °C

Procedure

A solution of tert.-Butyl hypochlorite (947 mg) in dichloromethane (15 mL) is added drop wise over a period of 1 h to a solution of trimethylene sulfide (0.63 mL) and 4-bromoaniline (1.50 g) in dichloromethane (60 mL) at −70° C. The reaction mixture is stirred for 15 min prior to the addition of a solution of 1,8-diazabycyclo[5.4.0]undec-7-ene (1.37 mL) in dichloromethane (10 mL). The reaction mixture is allowed to warm to −15° C. and quenched with water. The organic phase is separated, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20-40:60) to give the title compound. LC (method 1): tR=1.16 min; Mass spectrum (ESI+): m/z=244, 246 [M+H]+.

Workup

  1. customquenched with water
  2. customThe organic phase is separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20-40:60)

Sources & evidence

ORD record
ord-cf2df551af5b4b669edd70b101c9a5d3
Source dataset
uspto-grants-2016_08
Patent number
US09422312B2

Reaction notes

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