m-Chloroperbenzoic acid → HCID 59699464, compound

HRID 901082Notes

Reaction equation

HRID 901082 reaction equation
[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=2)[O:6][C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4]1.C1C=C(Cl)C=C(C(OO)=[O:30])C=1>ClCCl>[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH3:15])=[O:30])=[CH:12][CH:13]=2)[O:6][C:5]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:4]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11001103HCID 11001103, compound

Product 1

HCID 59699464HCID 59699464, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-22.5 °C

Procedure

To a solution of 23 (334.31 g, 1.11 mol) in anhydrous dichloromethane (5.46 L) at −30° C., mCPBA (255.29 g, 1.11 mol) in anhydrous dichloromethane (3.45 L) was added drop-wise over 2 hours. The reaction mixture was stirred at −20 to −25° C. for 3 hours under nitrogen atmosphere. The reaction mixture was quenched with saturated NaHCO3 (5.8 L) at −20° C. The organic layer was separated, washed with water (3×2 L), brine (2 L), dried over Na2SO4and concentrated to provide 358 g of crude desired product. 1H NMR (400 MHz, CD3OD) 2.80 (s, 3 H), 4.34-4.43 (m, 1H), 4.48-4.52 (m, 1H), 4.65-4.70 (m, 2H), 4.72-4.80 (m, 2H), 5.79 (d, J=8 Hz, 1 H), 7.45-7.48 (m, 2 H), 7.58-7.62 (m, 3H), 7.76-7.89 (m, 2H), 8.02-8.10 (m, 2H). The crude material was used directly in the next step.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 (5.8 L) at −20° C
  2. customThe organic layer was separated
  3. washwashed with water (3×2 L), brine (2 L)
  4. customdried over Na2SO4and
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-07897ed4aeb44f9088b814845313b239
Source dataset
uspto-grants-2008_04
Patent number
US07361689B2

Reaction notes

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