Carbon tetrabromide → 4-(6-Bromohexyl)-3-(3-ethoxy-3-oxopropyl)benzenepentanoic Acid Ethyl Ester

HRID 1648095Notes

Reaction equation

HRID 1648095 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]O)=[C:11]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:10]=1)[CH3:2].C(Br)(Br)(Br)[Br:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOCC>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Br:31])=[C:11]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 537219853-(3-Ethoxy-3-oxopropyl)-4-(6-hydroxyhexyl)benzenepentanoic acid ethyl ester

Product 1

HCID 542953904-(6-Bromohexyl)-3-(3-ethoxy-3-oxopropyl)benzenepentanoic Acid Ethyl EsterYield 75.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 0.673 g (1.65 mmol) of 3-(3-ethoxy-3-oxopropyl)-4-(6-hydroxyhexyl)benzenepentanoic acid ethyl ester from the preceding example, 1.1 g (3.3 mmol) of carbon tetrabromide, and 0.9 g (3.3 mmol) of triphenylphosphine in 25 mL of ether was stirred at room temperature for 23 hr. The mixture was diluted with 250 mL of ether, and the solution worked-up in the usual manner. The crude product was purified by flash chromatography on 80 g of silica gel, eluting with hexane-ethyl acetate (10:1). There was obtained 0.588 g (75.7%) of the title compound as a colorless oil.

Workup

  1. customThe crude product was purified by flash chromatography on 80 g of silica gel
  2. washeluting with hexane-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-32be5f95d38f4c4896a30df41147d917
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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