Dimethylformamide → 3-(4-Bromophenoxy)propan-1-ol

HRID 84994Notes

Reaction equation

HRID 84994 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH2:12][OH:13].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][CH2:12][OH:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78084-Bromophenol2×HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanol

Product 1

HCID 187610183-(4-Bromophenoxy)propan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 250 mL round bottom flask was added 4-bromophenol (16.5 g, 95.3 mmol), 3-bromopropanol (15.9 g, 114.4 mmol), N,N-dimethylformamide (50 mL) and potassium carbonate (22.4 g, 162.0 mmol). The reaction was allowed to stir at room temperature while being monitored by TLC(CH2Cl2). Upon the disappearance of 4-bromophenol the mixture was poured into a separatory funnel containing 50 mL of water. The product was extracted in diethyl ether and the organic layer was washed with 3×25-mL portions of cold water. The solvent was removed under reduced pressure. The product was purified by flash chromatography on silica gel eluting with dichloromethane. The solvent was removed under reduced pressure. Residual solvent and remaining 3-bromopropanol were removed in vacuo (14.2 g, 64.4%). 1H NMR (300 MHz, CDCl3) δ 7.35 (d, 9.0 Hz), 6.77 (d, J=9.0 Hz, 2H), 4.06 (t, J=6.0 Hz, 2H), 3.84 (t, J=6.0 Hz, 2H), 2.10 (q, J=6.0 Hz, 2H), 1.65 (s, 1H).

Workup

  1. extractionThe product was extracted in diethyl ether
  2. washthe organic layer was washed with 3×25-mL portions of cold water
  3. customThe solvent was removed under reduced pressure
  4. customThe product was purified by flash chromatography on silica gel eluting with dichloromethane
  5. customThe solvent was removed under reduced pressure
  6. customwere removed in vacuo (14.2 g, 64.4%)

Sources & evidence

ORD record
ord-a60f97a54a504337aa6010f816f94bc1
Source dataset
uspto-grants-2014_09
Patent number
US08846978B2

Reaction notes

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