Hydrogen Bromide → 3-difluoromethoxy-N-[2-(4-hydroxy-3-methoxyphenyl)-1-methylethyl]-2-(4-methylphenyl)acrylamide

HRID 1884266Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:18][C:19](=[O:33])[C:20]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)=[CH:21][O:22][CH:23]([F:25])[F:24])[CH3:17])=[CH:11][C:10]=1[O:34][CH3:35])C1C=CC=CC=1.Br>C(O)(=O)C>[F:24][CH:23]([F:25])[O:22][CH:21]=[C:20]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)[C:19]([NH:18][CH:16]([CH3:17])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([O:34][CH3:35])[CH:11]=1)=[O:33]

Participants

Conditions

Temperature: 80 °C

Procedure

1.80 g (3.74 mmol) of N-[2-(4-benzyloxy-3-methoxyphenyl)-1-methylethyl]-3-difluoromethoxy-2-(4-methylphenyl)acrylamide, 693 mg (4.11 mmol) of 48% hydrobromic acid and 20 ml of acetic acid were mixed and stirred at 80° C. for 2 hours. The solvent was distilled off from the reaction mixture under reduced pressure and the residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 1.10 g of 3-difluoromethoxy-N-[2-(4-hydroxy-3-methoxyphenyl)-1-methylethyl]-2-(4-methylphenyl)acrylamide.

Workup

distillationThe solvent was distilled off from the reaction mixture under reduced pressure

Sources & evidence

ORD record: ord-5e9b4c743abc4cc690d7f7a1f250b8c0
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06762321B2

Reaction notes

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