Hydrochloric Acid → HCID 21112931, compound
Reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11](C)[CH:10]=[CH:9][C:8]=1[S:14][CH3:15].[B:16](OC(C)C)([O:21]C(C)C)[O:17]C(C)C.Cl.[O:30]1CCC[CH2:31]1>>[CH3:31][O:30][C:11]1[CH:10]=[CH:9][C:8]([S:14][CH3:15])=[CH:7][C:12]=1[B:16]([OH:21])[OH:17]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
1.6M butyllithium in hexanes (3.5 ml, 5.6 mmol) was added dropwise to a stirred solution of 2-bromo-4-methylthioanisole (1.165 g, 5 mmol) in anhydrous tetrahydrofuran (30 ml) at −100° C. under nitrogen and stirred for 5 minutes then warmed to −78° C. for 1 hour. Triisopropyl borate (2.82 g, 15 mmol) was added dropwise and the mixture allowed to warm to room temperature. Hydrochloric acid (30 ml, 30 mmol) were added and the mixture stirred vigorously for 1 hour. The organic phase was separated, washed with brine, dried (MgSO4), evaporated to dryness and the residue purified on Biotage using ethyl acetate/iso-hexane (3:7) to yield the title compound as a white solid. (616 mg, 62%).
Workup
- temperatureto warm to room temperature
- stirringthe mixture stirred vigorously for 1 hour
- customThe organic phase was separated
- washwashed with brine
- dry with materialdried (MgSO4)
- customevaporated to dryness
- customthe residue purified on Biotage
Sources & evidence
- ORD record
- ord-7368678a1e5b4624a5f5485c388b008c
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07232821B2
Reaction notes
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