Potassium Bromide → HCID 54208139, compound

HRID 2402427Notes

Reaction equation

HRID 2402427 reaction equation
CC1(C)N([O])C(C)(C)CCC1.[OH:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:17]=1.[K+].[Br-].[O-]Cl.[Na+]>C(Cl)Cl>[O:12]=[CH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 253877Potassium BromideHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 53924309HCID 53924309, compound

Product 1

HCID 54208139HCID 54208139, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

TEMPO (0.02 equiv, 6 mg, 0.038 mmol) was added to a solution of methyl 2-(4-(3-hydroxypropyl)phenyl)acetate in CH2Cl2 (5 mL) and cooled to 0° C. KBr (2.2 equiv, 1.6 mL, 2.7M) and KHCO3 (5.5 equiv, 6.6 mL, 1.6M) solutions were then added followed by the dropwise addition of 10% aq. NaOCl (1.34 equiv, 1.9 g, 2.6 mmol). Once the addition was complete, the reaction was stirred for an additional 10 min. at 0° C. The reaction was quenched with sat. aq. sodium thiosulfate solution (3 mL) and then partitioned between H2O (10 mL) and CH2Cl2 (10 mL). The organic phase was separated and the remaining aqueous phase was extracted with EtOAc (2×2 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting aldehyde was carried forward to the subsequent reaction without further purification. LRMS: 206.1 (calc) 207.2 (found)(MH)+.

Workup

  1. additionOnce the addition
  2. customThe reaction was quenched with sat. aq. sodium thiosulfate solution (3 mL)
  3. custompartitioned between H2O (10 mL) and CH2Cl2 (10 mL)
  4. customThe organic phase was separated
  5. extractionthe remaining aqueous phase was extracted with EtOAc (2×2 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting aldehyde was carried forward to the subsequent reaction without further purification

Sources & evidence

ORD record
ord-cf7bb1c8d11b4114a21d9dd415639d03
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

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