Water → HCID 18620099, compound

HRID 1862606Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][O:10][CH2:11][O:12][CH3:13])[CH:5]=[CH:4][C:3]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cu][C:23]#[N:24].O>CN(C)C=O>[CH2:15]([O:14][C:3]1[CH:4]=[CH:5][C:6]([CH2:8][CH2:9][O:10][CH2:11][O:12][CH3:13])=[CH:7][C:2]=1[C:23]#[N:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirred solution of the obtained 4′-benzyloxy-3′-bromophenethyl alcohol (782 mg) in dichloromethane (8 ml) were added N,N-diisopropylethylamine (665 μl) and chloromethyl methyl ether (232 μl) under ice-cooling, and the mixture was stirred for 6 hours at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. After the extract was washed with brine, removal of the solvent under reduced pressure gave benzyl 2-bromo-4-(2-methoxymethoxyethyl)phenyl ether (804 mg). To a solution of benzyl 2-bromo-4-(2-methoxymethoxyethyl)phenyl ether (804 mg) in N,N-dimethylformamide (5 ml) was added copper(I) cyanide (458 mg) and the mixture was stirred for 2 days at 120° C. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, and removal of the solvent under reduced pressure gave 2-benzyloxy-5-(2-methoxymethoxyethyl)benzonitrile (711 mg).

Workup

extractionextracted with ethyl acetate
washThe extract was washed with brine, and removal of the solvent under reduced pressure

Sources & evidence

ORD record: ord-832cc2383e4a4952aa74dbe5f5ddfe7f
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06538152B1

Reaction notes

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