Acetyl chloride → HCID 58764041, compound

HRID 1438216Notes

Reaction equation

HRID 1438216 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[Br:12][C:13]1[C:18]([O:19][CH2:20][CH3:21])=[CH:17][C:16]([OH:22])=[C:15]([CH2:23][CH3:24])[CH:14]=1>C(Cl)Cl>[Br:12][C:13]1[C:18]([O:19][CH2:20][CH3:21])=[CH:17][C:16]([O:22][C:1](=[O:3])[CH3:2])=[C:15]([CH2:23][CH3:24])[CH:14]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58764135HCID 58764135, compound

Product 1

HCID 58764041HCID 58764041, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.91 mL, 12.8 mmol) followed by triethylamine (1.8 mL, 12.8 mmol) were added to a stirred solution of 4-bromo-5-ethoxy-2-ethyl-phenol (2.6 g, 10.7 mmol) dissolved in CH2Cl2 (20 mL). The reaction was stirred for 45 mins and then partitioned between 1N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine dried over Na2SO4 and concentrated. Purification by flash column chromatography (0% to 20% EtOAc in hexanes) gave the product as a clear oil (1.64 g, 53%). 1H NMR (400 MHz, CDCl3): δ 1.16 (t, J=7.6 Hz, 3H), 1.45 (t, J=7.1 Hz, 3H), 2.31 (s, 3H), 2.45 (q, J=7.6 Hz, 2H), 4.05 (q, J=7.1 Hz, 2H), 6.58 (s, 1H), 7.41 (s, 1H).

Workup

  1. custompartitioned between 1N HCl and EtOAc
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (0% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-171ae92446454cfb9ef710b0e7526399
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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