Potassium Bromide → HCID 59271830, compound

HRID 1893194Notes

Reaction equation

HRID 1893194 reaction equation
C(=O)(O)[O-].[Na+].[Br-].[K+].[Si:8]([O:15][CH2:16][C:17]([O:23][CH3:24])([CH3:22])[CH2:18][CH2:19][CH2:20][OH:21])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].CC1(C)N([O])C(C)(C)CCC1.[O-]Cl.[Na+]>O.C(Cl)Cl>[Si:8]([O:15][CH2:16][C:17]([O:23][CH3:24])([CH3:22])[CH2:18][CH2:19][CH:20]=[O:21])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:9])[CH3:10]

Participants

8

Reactant 5

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 59271809HCID 59271809, compound

Product 1

HCID 59271830HCID 59271830, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of sodium bicarbonate (627 g, 74.6 mol) and potassium bromide (672 g, 56.5 mol) in water (20 L) was added 5-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxy-4-methylpentan-1-ol (3.5 kg, 11.2 mol), DCM (10 L), TEMPO (17.6 g, 113 mol). The resulting mixture was cooled to <5° C. and NaOCl (13% solution, total 6.7 L, 14.6 mol) was added in portions via a funnel while maintaining the reaction temperature <5° C. The mixture was stirred 6 hours warming to ambient temperature. The organic layer was collected. The aqueous layer was extracted with 4 L DCM. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude material, 4.2 kg, was used in the next step without further purification. 1H NMR (300 MHz, CDCl3): δ 9.75 (t, J=1.8 Hz, 1 H); 3.43 (q, J=10.4 Hz, 2H); 3.17 (s, 3H); 2.43 (t, J=1.8 Hz, 2H); 2.02-1.65 (m, 2 H); 0.99-0.71 (s, 9H); 0.14 (s, 6H).

Workup

  1. temperatureThe resulting mixture was cooled to <5° C.
  2. temperaturewhile maintaining the reaction temperature <5° C
  3. customThe organic layer was collected
  4. extractionThe aqueous layer was extracted with 4 L DCM
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material, 4.2 kg, was used in the next step without further purification

Sources & evidence

ORD record
ord-cdf6f5a76ed3449dac868b464dabe37a
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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