Triethylamine → HCID 15485563, compound

HRID 367249Notes

Reaction equation

[Br:1][C:2]1[C:3]2[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=2[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.CCN(CC)CC.FC(F)(F)S(O[Si:31]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33])(=O)=O>CN(C=O)C>[CH:32]([Si:31]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[O:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]2[S:5][C:4]3[CH:14]=[CH:15][CH:16]=[CH:17][C:3]=3[C:2]=2[Br:1])=[CH:12][CH:11]=1)([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-bromo-2-(4-hydroxyphenyl)benzo[b]-thiophene (9.4 g, 30.8 mmol) in 50 mL of dry DMF was treated with Et3N (6.3 g, 61.6 mmol) and cooled to 0° C. To this was added in a dropwise manner 14.2 g (46.2 mmol) triisopropylsilyl trifluoromethanesulfonate. The cooling bath was removed and the reaction allowed to stir at ambient temperature for 2 h before pouring into 100 mL brine. This was extracted with EtOAc (2×50 mL). The combined extracts were washed with brine (2×100 mL), dried over MgSO4 and concentrated under reduced pressure to 4.8 g of an oil. The crude product was purified by chromatography (SiO2 ; hexanes) to recover 11.7 g (25.4 mmol, 82%) of the desired product as a white solid.

Workup

customThe cooling bath was removed
additionbefore pouring into 100 mL brine
extractionThis was extracted with EtOAc (2×50 mL)
washThe combined extracts were washed with brine (2×100 mL)
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure to 4.8 g of an oil
customThe crude product was purified by chromatography (SiO2 ; hexanes)

Sources & evidence

ORD record: ord-384c9ad2a40247abb886a7bb5feefbfe
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133262

Reaction notes

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