Bromine → 4-(5-Bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester

HRID 2106036Notes

Reaction equation

HRID 2106036 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([OH:23])([C:19]([F:22])([F:21])[F:20])[CH2:6][C:7]([C:10]1[C:18]2[O:17][CH2:16][CH2:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)([CH3:9])[CH3:8])[CH3:2].[Br:25]Br>C(O)(=O)C.C(=O)(O)[O-].[Na+]>[CH2:1]([O:3][C:4](=[O:24])[C:5]([OH:23])([C:19]([F:21])([F:22])[F:20])[CH2:6][C:7]([C:10]1[C:18]2[O:17][CH2:16][CH2:15][C:14]=2[CH:13]=[C:12]([Br:25])[CH:11]=1)([CH3:9])[CH3:8])[CH3:2]

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 469391194-(2,3-Dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester

Product 1

HCID 589599534-(5-Bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 10 g (29 mmol) of 4-(2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester in 20 mL of acetic acid (HOAc) was added dropwise a solution of 1.55 mL (30 mmol) of bromine in 10 nL of HOAc. The reaction was monitored by proton NMR. An additional 0.5 mL of Br2 was added. The mixture was diluted with saturated aqueous sodium bicarbonate and extracted with diethyl ether. The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford 11.7 g (95%) of 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a3c088142434a30bdd0d3302ef5eb5b
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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