tert-Butyl bromoacetate → (4-Hydroxy-2-methyl-phenylsulfanyl)-acetic acid tert-butyl ester

HRID 1242312Notes

Reaction equation

HRID 1242312 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[C:10]([O:14][C:15](=[O:18])[CH2:16]Br)([CH3:13])([CH3:12])[CH3:11].C(N(C(C)C)C(C)C)C.Cl.CCOC(C)=O>C1COCC1.O>[C:10]([O:14][C:15](=[O:18])[CH2:16][S:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 79177tert-Butyl bromoacetateHCID 81531DiisopropylethylamineHCID 102194784-Mercapto-3-methylphenolHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 67072245(4-Hydroxy-2-methyl-phenylsulfanyl)-acetic acid tert-butyl esterYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10 g (71 mmol) of 4-mercapto-3-methyl-phenol (DE 2101359) and 10.5 ml (1 eq., 71 mmol) of bromo-acetic acid tert-butyl ester in 250 ml of THF was treated at room temperature with 12.2 ml (1 eq., 71 mmol) of N-ethyldiisopropylamine. The suspension was heated at reflux for 1 h, cooled to ambient temperature, and treated with water. The reaction mixture was then poured onto 0.1 M HCl/AcOEt, the organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Purification by flash chromatography (SiO2, heptane/toluene/AcOEt=10/1/1) afforded finally 5.6 g of the title product as white solid.

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 1 h
  3. customthe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customPurification by flash chromatography (SiO2, heptane/toluene/AcOEt=10/1/1)

Sources & evidence

ORD record
ord-38476e3f88f8465c953b2cb3fa8e8911
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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