Triethylamine → HCID 13170366, compound

HRID 736860Notes

Reaction equation

HRID 736860 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].C(N(CC)CC)C.[Si:32]([O:39][C:40]1[CH:47]=[CH:46][C:43](C=O)=[CH:42][CH:41]=1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>ClCCl>[Br:21][C:20]([Br:24])=[CH:1][C:47]1[CH:46]=[CH:43][CH:42]=[CH:41][C:40]=1[O:39][Si:32]([C:35]([CH3:36])([CH3:37])[CH3:38])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

Product 1

HCID 13170366HCID 13170366, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (3.44 g, 13.1 mmol) was dissolved in dichloromethane (25 ml) in nitrogen atmosphere, carbon tetrabromide (2.18 g, 6.56 mmol) was added little by little under cooling with ice, and triethylamine (4.4 ml, 26.2 mmol) was dropwise added, followed by stirring for 10 minutes. Then, under cooling with ice, a dichloromethane solution (20 ml) of 4-(tert-butyldimethylsilyloxy)benzaldehyde (10.0 g, 73.4 mmol) prepared in 1) was dropwise added, followed by stirring for 1 hour. Silica gel (50 g) was added to the reaction solution, the reaction solution was concentrated under reduced pressure to dryness, and the resulting product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1, containing 0.1% v/v triethylamine) to give 1,1-dibromo-2-(tert-butyldimethylsilyloxyphenyl)ethylene (2.77 g, 81%) as a pale yellow oily substance.

Workup

  1. additionwas added little by little
  2. additionwas dropwise added
  3. temperatureThen, under cooling with ice
  4. additionwas dropwise added
  5. stirringby stirring for 1 hour
  6. additionSilica gel (50 g) was added to the reaction solution
  7. concentrationthe reaction solution was concentrated under reduced pressure to dryness
  8. customthe resulting product was purified by silica gel column chromatography (hexane
  9. additionethyl acetate=20:1, containing 0.1% v/v triethylamine)

Sources & evidence

ORD record
ord-48d234ce93d74c7181df844808c40222
Source dataset
uspto-grants-2009_09
Patent number
US07595415B2

Reaction notes

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