Boron tribromide → HCID 58779365, compound

HRID 1372150Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([CH:18]=[O:19])=[C:13]3[C:17]=2[S:16][CH:15]=[CH:14]3)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([CH:18]=[O:19])=[C:13]3[C:17]=2[S:16][CH:15]=[CH:14]3)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a 50 ml round bottom flask was added 7-(4-methoxyphenyl)-1-benzothiophene-4-carbaldehyde (420 mg, 1.57 mmol) to CH2Cl2 (8.5 ml) and the solution was cooled to −78° C. To the solution was added BBr3 (3.14 ml of 1.0 M in CH2Cl2, 3.13 mmol) dropwise as the reaction turned dark red in color. The reaction was warmed to ambient temperature as it turned dark green and was complete in 1 h by TLC. After the reaction was quenched with water (15 ml) it was extracted with ether and the organic were combined, dried over anhydrous Na2SO4 and concentrated to 460 mg (>95%) product as a slightly impure green solid. Reverse phase HPLC (CH3CN/water with 0.1% TFA) was used to obtain an analytical sample (120 mg) as a slightly yellow solid: mp 202–204° C.; 1H NMR (300 MHz, DMSO-d6): δ 6.97 (2H, d, J=8.5 Hz), 7.60 (1H, d, J=7.6), 7.64 (2H, d, J=8.5 Hz), 8.10 (1H, d, J=7.6 Hz), 8.14 (1H, d, J=5.6 Hz), 8.38 (1H, d, J=5.6 Hz), 9.92 (1H, s), 10.29 (1H, s); MS (ESI) m/z 253 ([M−H]).

Workup

temperatureThe reaction was warmed to ambient temperature as it
customAfter the reaction was quenched with water (15 ml) it
extractionwas extracted with ether
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated to 460 mg (>95%) product as a slightly impure green solid
customto obtain an analytical sample (120 mg) as a slightly yellow solid

Sources & evidence

ORD record: ord-ad5877d3615b47cb8727caa58fb39107
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157491B2

Reaction notes

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