Hydrogen Peroxide → HCID 66892729, compound

HRID 452452Notes

Reaction equation

HRID 452452 reaction equation
C1(B2[O:12][CH2:11][C:10]3[CH:13]=[CH:14][C:15]([S:17][C:18]([F:21])([F:20])[F:19])=[CH:16][C:9]=3[O:8]2)C=CC=CC=1.OO.OCC1C(SC(F)(F)F)=CC=CC=1O>C1COCC1>[OH:12][CH2:11][C:10]1[CH:13]=[CH:14][C:15]([S:17][C:18]([F:19])([F:20])[F:21])=[CH:16][C:9]=1[OH:8]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 66887274HCID 66887274, compoundHCID 67155707HCID 67155707, compound

Product 1

HCID 66892729HCID 66892729, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-phenyl-7-[(trifluoromethyl)thio]-4H-1,3,2-benzodioxaborinin (14.0 g, 44 mmol) and H2O2 (30% in water, 27.0 ml, 264 mmol) in THF (100 ml) was stirred at ambient temperature for 3 h, before it was quenched at 0° C. with a aquous solution of Na2SO3 (19.0 g). The mixture was acidified with HCl (10%), extracted with EtOAc and the combined organic layers were evaporated to dryness (no drying agent). The crude product was purified on flash column chromatography (isooctane/EtOAc 4:1 and isooctane/EtOAc 7:3) to afford two different fractions. One fraction with the stereoisomer as a by-product, 2-(hydroxymethyl)-3-[(trifluoromethyl)thio]phenol (4.1 g) and one with the title product (2.75 g). 1H-NMR (400 MHz, MeOH): δ 7.40 (1H, d, J 8.0 Hz), δ 7.13 (1H, d, J 8.0 Hz), δ 7.12 (1H, s), δ 4.66 (2H, s).

Workup

  1. customwas quenched at 0° C. with a aquous solution of Na2SO3 (19.0 g)
  2. extractionextracted with EtOAc
  3. customthe combined organic layers were evaporated to dryness (no drying agent)
  4. customThe crude product was purified on flash column chromatography (isooctane/EtOAc 4:1 and isooctane/EtOAc 7:3)
  5. customto afford two different fractions

Sources & evidence

ORD record
ord-872d20b4e5894b02b1d898c9cc1814d4
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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