3-(4-Fluorobenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylboronic acid → 3-{4-hydroxy-3-[3-(4-fluorobenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic Acid
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([O:13]CC)=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[F:16][C:17]1[CH:41]=[CH:40][C:20]([CH2:21][O:22][C:23]2[C:24](B(O)O)=[CH:25][C:26]3[C:27]([CH3:36])([CH3:35])[CH2:28][CH2:29][C:30]([CH3:34])([CH3:33])[C:31]=3[CH:32]=2)=[CH:19][CH:18]=1>>[OH:8][C:7]1[CH:2]=[CH:3][C:4]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])=[CH:5][C:6]=1[C:24]1[C:23]([O:22][CH2:21][C:20]2[CH:40]=[CH:41][C:17]([F:16])=[CH:18][CH:19]=2)=[CH:32][C:31]2[C:30]([CH3:34])([CH3:33])[CH2:29][CH2:28][C:27]([CH3:36])([CH3:35])[C:26]=2[CH:25]=1Participants
3
Procedure
In a manner similar of Example 1(c), by reaction of 1.0 g (3.7 mmol) of ethyl 3-(3-bromo-4-hydroxyphenyl)acrylate obtained in Example 34(d) with 1.97 g (5.5 mmol) of 3-(4-fluorobenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylboronic acid obtained above, 825 mg (44%) of the expected compound were obtained in the form of a white solid having a melting point of 123°-125° C.
Sources & evidence
- ORD record
- ord-69eb92d1c78549a3b25f8d4e5b5bc2b9
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06632963B1
Reaction notes
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