Phenethyl bromide → HCID 22716779, compound

HRID 1583025Notes

Reaction equation

HRID 1583025 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:10]([C:12]1[CH:20]=[C:16]([C:17]([OH:19])=[O:18])[C:15]([OH:21])=[CH:14][CH:13]=1)=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[C:4]1([CH2:3][CH2:2][O:21][C:15]2[CH:14]=[CH:13][C:12]([CH:10]=[O:11])=[CH:20][C:16]=2[C:17]([O:19][CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:18])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 10796Cesium carbonateHCID 692265-Formylsalicylic acid

Product 1

HCID 22716779HCID 22716779, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

(2-Bromoethyl)benzene (41 mL, 0.3 mol, 5 eq) was added to a stirred solution of 5-formylsalicylic acid (10 g, 0.06 mol, 1 eq), tetra-n-butylammonium iodide (44 g, 0.12 mol, 2 eq) and cesium carbonate (39 g, 0.12 mol, 2 eq) in N,N-dimethylformamide (200 mL). The reaction mixture was stirred for 4 days, then concentrated in vacuo. The residue was diluted with ethyl acetate (200 mL) and the organic solution washed with water (200 mL), 1M HCl (2×200 mL), 1M sodium hydroxide (2×200 mL) and then brine (200 mL), dried over sodium sulfate and evaporated in vacuo to give a brown oil. The product was not purified further, but taken immediately onto the next step. RF (petroleum ether:ethyl acetate, 1:1) 0.88. 1H NMR (CDCl3) δ9.88 (s, 1H, O═C—H), 8.23 (d, 1H, J 2.2 Hz, ArH), 7.98 (dd, 1H, J 8.7 and 2.2 Hz, ArH), 7.06 (d, 1H, J 8.7 Hz, ArH), 4.56 (t, 2H, J 7.2 Hz, OCH2CH2Ph), 4.33 (t, 2H, J 7.2 Hz, OCH2CH2Ph), 3.11 (t, 2H, J 7.2 Hz, OCH2CH2Ph), 3.03 (t, 2H, J 7.2 Hz, OCH2CH2Ph).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate (200 mL)
  3. washthe organic solution washed with water (200 mL), 1M HCl (2×200 mL), 1M sodium hydroxide (2×200 mL)
  4. dry with materialbrine (200 mL), dried over sodium sulfate
  5. customevaporated in vacuo
  6. customto give a brown oil
  7. customThe product was not purified further

Sources & evidence

ORD record
ord-337290f436914ca998f2c65ec710d84f
Source dataset
uspto-grants-2004_05
Patent number
US06740670B2

Reaction notes

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