Bromine → 7-(5-Bromo-2-hydroxy-3,4,6-trimethylphenyl)-7-(4-fluorophenyl)heptanoic acid

HRID 373378Notes

Reaction equation

HRID 373378 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[C:19]([CH3:25])[C:18]=2[OH:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.[Br:27]Br>C(O)(=O)C>[Br:27][C:21]1[C:20]([CH3:24])=[C:19]([CH3:25])[C:18]([OH:26])=[C:17]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[C:22]=1[CH3:23]

Participants

4

Reactant 2

HCID 24408BromineHCID 110247607-(4-Fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoic acid

Product 1

HCID 151251227-(5-Bromo-2-hydroxy-3,4,6-trimethylphenyl)-7-(4-fluorophenyl)heptanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 7-(4-fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoic acid (1.32 g) in acetic acid (10 ml) was added dropwise a solution of bromine (0.19 ml) in acetic acid (2 ml) with ice cooling. After completion of addition, the mixture was stirred at room temperature for 30 minutes. The reaction mixture was extracted by addition of water and ethyl acetate. The organic layer was separated and washed in turn with water and saturated saline and dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to obtain 7-(5-bromo-2-hydroxy-3,4,6-trimethylphenyl)-7-(4-fluorophenyl)heptanoic acid (1.04 g) (Compound 12). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. additionAfter completion of addition
  2. extractionThe reaction mixture was extracted by addition of water and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed in turn with water and saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-45b482e42f6349448dcf97921a887780
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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