4-Bromophenol → HCID 59589836, compound

HRID 1472826Notes

Reaction equation

HRID 1472826 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][N:10]([CH3:15])[CH2:11][C@@H:12](O)[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C@H:12]([CH3:13])[CH2:11][N:10]([CH3:15])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 6950248(S)-(+)-1-Dimethylamino-2-propanol

Product 1

HCID 59589836HCID 59589836, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromophenol (0.2 g, 1.16 mmol) and (S)-(+)-1-dimethylamino-2-propanol (0.14 ml, 1.16 mmol) were dissolved in dichloromethane (10 ml). PS-Triphenylphospine (1.74 g, 1.74 mmol) was added, followed by di-tert-butyl azodicarboxylate (0.4 g, 1.74 mmol). The mixture was stirred overnight at room temperature, then filtered and the filtrate washed with sodium hydrogenocarbonate then brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the desired product. Yield: 0.3 g, 100%. LCMS method: 2, RT: 2.62 min; MI: 258-260 [M+1].

Workup

  1. filtrationfiltered
  2. washthe filtrate washed with sodium hydrogenocarbonate
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7ca488f5c1c4465b97c54ffe556a044
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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