2-Chlorobenzoxazole → 4-(Benzoxazol-2-yl)benzyl alcohol
Reaction equation
C([Li])CCC.Br[C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1.Cl[C:16]1[O:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1>C1COCC1>[O:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To 500 ml THF cooled to -78° C. is added butyl lithium (2 eq.) followed by 4-bromobenzyl alcohol (27.2 g; 145 mmol) slowly over 45 minutes in a solution of THF (100 ml) keeping the temperature below -72° C. After 10 minutes following the final addition of the alcohol is added 2-chlorobenzoxazole (23.3 g; 145 mmol) in 25 ml THF slowly over 45 minutes. The temperature is maintained at -78° C. for 1 hour and then warmed to -40° C. for 15 minutes. The reaction is then quenched with 15 ml of acetic acid and allowed to warm to room temperature, diluted with 800 ml ether, washed 3x with H2O and brine, dried (MgSO4) and concentrated in vacuo to obtain a brown oily solid which is washed with 400 ml petroleum ether and filtered to obtain 4-(benzoxazol-2-yl)benzyl alcohol as a tan solid which is used directly in Step B.
Workup
- customthe temperature below -72° C
- temperaturewarmed to -40° C. for 15 minutes
- customThe reaction is then quenched with 15 ml of acetic acid
- temperatureto warm to room temperature
- additiondiluted with 800 ml ether
- washwashed 3x with H2O and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customto obtain a brown oily solid which
- washis washed with 400 ml petroleum ether
- filtrationfiltered
Sources & evidence
- ORD record
- ord-d7d5b124225c43ae933c80490a3c2f3a
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05534532
Reaction notes
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