Sodium Chloride → HCID 59664574, compound

HRID 271039Notes

Reaction equation

HRID 271039 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([Si:9]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32]C)[CH:27]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16]C)[CH:11]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.[OH-].[Na+].[Na+].[Cl-]>C(Cl)Cl>[OH:16][C:12]1[CH:11]=[C:10]([Si:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([OH:2])[CH:4]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 59664572HCID 59664572, compound

Product 1

HCID 59664574HCID 59664574, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tetrakis (3-methoxyphenyl) silane (4.5 g, 0.001 mol) in CH2Cl2 (80 ml) was added BBr3 (50 ml of 1M CH2Cl2 solution) dropwise at −78° C. The mixture was allowed to room temperature and stirred overnight. The reaction mixture was poured into 2N NaOH 50 ml), and extracted with CH2Cl2. The aqueous layer was acidified with 5N HCl, and extracted with ethyl acetate. The organic layer was dried with MgSO4 and evaporated to give brown solid. Yield 95%. 1 H NMR (acetone) 6.95 ppm (CH aromatic), 6.98 ppm (CH aromatic), 7.2 ppm (CH aromatic), 7.4 ppm (CH aromatic), 8.4 (OH). IR (NaCl plate) 3300 cm−1, 3600 cm−1 (O—H).

Workup

  1. customwas allowed to room temperature
  2. extractionextracted with CH2Cl2
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried with MgSO4
  5. customevaporated
  6. customto give brown solid

Sources & evidence

ORD record
ord-33b77e86fe0f49faacd2dbfef554affc
Source dataset
uspto-grants-2008_11
Patent number
US07452658B2

Reaction notes

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