Water → HCID 66705014, compound

HRID 424368Notes

Reaction equation

HRID 424368 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:3]=1[CH2:4][OH:5].C(N(C(C)C)CC)(C)C.[CH3:21][O:22][CH2:23]Cl.O>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:3]=1[CH2:4][O:5][CH2:21][O:22][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 534078974-Bromo-3-(hydroxymethyl)benzonitrile

Product 1

HCID 66705014HCID 66705014, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-5-cyanobenzyl alcohol (4.59 g, 21.7 mmol) in dichloromethane (80 mL) were added diisopropylethylamine (5.6 mL, 32 mmol) and chloromethyl methyl ether (2.3 mL, 30 mmol) at 0° C., and the reaction mixture was stirred at room temperature overnight. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (6:1 hexane/ethyl acetate) to give 18f (4.08 g, 71%): 1H NMR (300 MHz, CDCl3) δ (ppm) 3.43 (s, 3H), 4.65 (s, 2H), 4.80 (s, 2H), 7.43 (dd, J=8.2, 4.1 Hz, 1H), 7.66 (d, J=8.2 Hz, 1H), 7.82 (d, J=4.1 Hz, 1H).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (6:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ef32e5090ddc4e4b932ad0809413b16d
Source dataset
uspto-grants-2012_01
Patent number
US08106031B2

Reaction notes

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