Sodium Chloride → HCID 19431315, compound

HRID 1077406Notes

Reaction equation

HRID 1077406 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[O:16]C)[CH2:12][CH:11]=[C:10]2[C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=1.CCOC(C)=O.[Na+].[Cl-]>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[OH:16])[CH2:12][CH:11]=[C:10]2[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 19431302HCID 19431302, compound

Product 1

HCID 19431315HCID 19431315, compoundYield 115.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of BBr3 in CH2Cl2 (1.0M, 9.60 ml, 9.60 mmol) is added dropwise to a solution of 5,6-dimethoxy-3-(4-methoxyphenyl)indene (0.60 g, 2.23 mmol) in 2 ml of CH2Cl2, cooled to -70° C. The red solution obtained is heated at room temperature and stirred for 1 h at this temperature. The reaction mixture is poured into a mixture of ice-water and AcOEt. The aqueous phase is saturated with NaCl then extracted twice with AcOEt. The organic phases collected are washed with saturated aqueous NaCl solution, dried over MgSO4 and evaporated to dryness to give a red solid (0.62 g) which is used directly in the following step.

Workup

  1. customThe red solution obtained
  2. temperatureis heated at room temperature
  3. extractionthen extracted twice with AcOEt
  4. customThe organic phases collected
  5. washare washed with saturated aqueous NaCl solution
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-1591f541e0544c4b9cb621a3d3e2a56e
Source dataset
uspto-grants-1996_08
Patent number
US05543298

Reaction notes

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