Thionyl Chloride → HCID 66777958, compound

HRID 2091172Notes

Reaction equation

HRID 2091172 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:13]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)O.S(Cl)([Cl:23])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:13]([Cl:23])[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 66777987HCID 66777987, compound

Product 1

HCID 66777958HCID 66777958, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution (20 mL) of (3-bromo-5-methoxy-1-benzofuran-2-yl)(cyclohexyl)methanol (1.82 g) synthesized above in toluene was added thionyl chloride (469 μL) and the mixture was stirred at 100° C. for 1.5 hr. The reaction mixture was poured into ice-cooled saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (1.73 g, 90%) as a yellow solid.

Workup

  1. additionThe reaction mixture was poured into ice-
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e2118fc61d7d4c5eb368bddc8845866c
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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