Bromotrimethylsilane → 4-Bromomethyl-2'-(methoxycarbonyl)amino-1,1'-biphenyl

HRID 1974597Notes

Reaction equation

HRID 1974597 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16]([O:18][CH3:19])=[O:17])=[CH:5][CH:4]=1.[Br:20][Si](C)(C)C>C(Cl)Cl>[Br:20][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16]([O:18][CH3:19])=[O:17])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 218367054-Hydroxymethyl-2'-(methoxycarbonyl)amino-1,1'-biphenyl

Product 1

HCID 218365754-Bromomethyl-2'-(methoxycarbonyl)amino-1,1'-biphenylYield 63.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-hydroxymethyl-2'-(methoxycarbonyl)amino-1,1'-biphenyl (239 mg, 0.93 mmol) in methylene chloride (4 mL) was treated with bromotrimethylsilane (3.0 mL, 22.7 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with additional methylene chloride and washed with saturated aqueous sodium chloride. After drying over magnesium sulfate, the filtered organic layer was evaporated under vacuum The residue was purified by preparative thin layer chromatography on silica gel, eluting with methylene chloride/methanol (100:3) to give 190 mg of the product.

Workup

  1. washwashed with saturated aqueous sodium chloride
  2. dry with materialAfter drying over magnesium sulfate
  3. customthe filtered organic layer was evaporated under vacuum The residue
  4. customwas purified by preparative thin layer chromatography on silica gel
  5. washeluting with methylene chloride/methanol (100:3)

Sources & evidence

ORD record
ord-c6e911fe71554e1889a3a0d50c68da41
Source dataset
uspto-grants-1994_02
Patent number
US05283241

Reaction notes

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