Ethyl Acetate → {4-t-Butyl-3-[2-(9H-xanthen-9-yl)acetamido]phenyl}-methyltriphenylphosphonium bromide

HRID 1734918Notes

Reaction equation

HRID 1734918 reaction equation
C(Br)(Br)(Br)[Br:2].[C:6]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][C:11]=1[NH:18][C:19](=[O:35])[CH2:20][CH:21]1[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:28][C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)([CH3:9])([CH3:8])[CH3:7].[C:36]1([P:42]([C:49]2C=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[C:55](OCC)(=O)C>C(Cl)Cl>[Br-:2].[C:6]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[P+:42]([CH3:55])([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:12][C:11]=1[NH:18][C:19](=[O:35])[CH2:20][CH:21]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[O:28][C:29]2[C:34]1=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH3:7])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22078730N-(2-t-butyl-5-hydroxymethylphenyl)-2-(9H-xanthen-9-yl)acetamide

Product 1

HCID 86749635{4-t-Butyl-3-[2-(9H-xanthen-9-yl)acetamido]phenyl}-methyltriphenylphosphonium bromideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.19 g (9.63 mmol) of carbon tetrabromide were added to a solution of 2.57 g (6.40 mmol) of N-(2-t-butyl-5-hydroxymethylphenyl)-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 14) and 2.04 g (7.77 mmol) of triphenylphosphine in 20 ml of methylene chloride, and the resulting mixture was stirred for 4 hours at room temperature. At the end of this time, the reaction mixture was placed on a column containing 100 g of silica gel and the column was eluted with a 1:9 by volume mixture of diethyl ether and methylene chloride. The eluates were combined and concentrated by evaporation under reduced pressure, to give 2.52 g (yield 85%) of the title bromide as crystals, melting at 229°-231° C. (after recrystallization from ethyl acetate).

Workup

  1. additioncontaining 100 g of silica gel
  2. washthe column was eluted with a 1:9 by volume mixture of diethyl ether and methylene chloride
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customto give

Sources & evidence

ORD record
ord-998ae86b7731414d9806f1dc28979e8e
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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