Bromine → 3-[(4-Bromo-2,5-dimethylphenyl)thio]propanoic acid

HRID 1602773Notes

Reaction equation

HRID 1602773 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[Br:15]Br>ClCCl>[Br:15][C:6]1[C:5]([CH3:8])=[CH:4][C:3]([S:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 167883143-(2,5-Dimethyl-phenylsulfanyl)-propionic acid

Product 1

HCID 196075383-[(4-Bromo-2,5-dimethylphenyl)thio]propanoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
5 °C

Procedure

25.23 g (0.12 mol) of the title compound of Example 1, Step A was dissolved in 250 mL of dichloromethane and cooled to 5° C. A solution of 19.12 g (0.12 mol) of bromine in 25 mL of dichloromethane was added dropwise over 45 minutes, keeping the reaction temperature at 5° C. The reaction was then allowed to warm to room temperature, diluted with 200 mL of dichloromethane and washed twice with 400 mL of water. The organice layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield 34.35 g of the title compound of step A as a white solid melting at 105-107° C. 1H NMR (CDCl3): δ2.33 (s,3H), 2.34 (s, 3H), 2.67 (t, 2H), 3.10 (t, 2H), 7.18 (s, 1H), 7.36 (s, 1H).

Workup

  1. customat 5° C
  2. temperatureto warm to room temperature
  3. washwashed twice with 400 mL of water
  4. customThe organice layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ded7d574ea9484d809cdf4bae618c6e
Source dataset
uspto-grants-1999_11
Patent number
US05985799

Reaction notes

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