Acetic Acid → 3-(8-Acetoxy-9-bromononyl)-1-methylthymine

HRID 361524Notes

Reaction equation

HRID 361524 reaction equation
[OH:1][CH:2]([CH2:20]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[CH:13][N:12]([CH3:18])[C:11]1=[O:19].[BrH:22].[C:23]([OH:26])(=O)[CH3:24].C(=O)(O)[O-].[Na+]>ClCCl>[C:23]([O:1][CH:2]([CH2:20][Br:22])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[CH:13][N:12]([CH3:18])[C:11]1=[O:19])(=[O:26])[CH3:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 232879543-(8,9-Dihydroxynonyl)-1-methylthymine

Product 1

HCID 232959773-(8-Acetoxy-9-bromononyl)-1-methylthymineYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(8,9-dihydroxynonyl)-1-methylthymine (2.16 g, 7.6 mmol) and a 30% solution of hydrogen bromide in acetic acid (4.5 mL, 23 mmol ) was stirred for 1 hour. The reaction was added slowly to a beaker containing sodium bicarbonate (8.4 g, 0.1 mol), ice water (30 mL), and dichloromethane (30 mL). The layers were separated and the aqueous layer extracted with dichloromethane (2×60 mL). The combined organic layers were washed with water (30 mL), saturated aqueous salt solution (30 mL), and dried over sodium sulfate. The solvent was removed to yield 2.59 g (85% yield) 3-(8-acetoxy-9-bromononyl)-1-methylthymine (inventive compound no. 1908) as a thick, slightly orange oil.

Workup

  1. additionThe reaction was added slowly to a beaker
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with dichloromethane (2×60 mL)
  4. washThe combined organic layers were washed with water (30 mL), saturated aqueous salt solution (30 mL)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-abb7c4eaed674d7a955ff2c48421db1a
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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