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Chemical Structure| 6968-28-1
Chemical Structure| 6968-28-1
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Product Details of [ 6968-28-1 ]

CAS No. :6968-28-1 MDL No. :MFCD00043538
Formula : C8H5BrO4 Boiling Point : -
Linear Structure Formula :- InChI Key :AZXKGUVDIORSED-UHFFFAOYSA-N
M.W : 245.03 Pubchem ID :81428
Synonyms :

Safety of [ 6968-28-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6968-28-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 6968-28-1 ]
  • Downstream synthetic route of [ 6968-28-1 ]

[ 6968-28-1 ] Synthesis Path-Upstream   1~9

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  • [ 64169-34-2 ]
Reference: [1] Patent: CN107082769, 2017, A,
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  • [ 6968-28-1 ]
  • [ 6941-75-9 ]
Reference: [1] Helvetica Chimica Acta, 2004, vol. 87, # 4, p. 825 - 844
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 5738 - 5746
[3] Patent: CN107082769, 2017, A,
  • 3
  • [ 6968-28-1 ]
  • [ 86-90-8 ]
YieldReaction ConditionsOperation in experiment
84% at 140℃; for 2 h; A solution of 4-bromophthalic acid (5 g, 0.02 mol) and acetic anhydride (30 mL) was heated for 2 h at 140 °C.
The reaction mixture was cooled to room temperature and the excess of acetic anhydride was removed under reduced pressure.
The residue was washed with petroleum ether and then 4-bromophthalic anhydride was obtained as white solid. Yield: 3.8 g, 84percent, mp: 104-106 °C.
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 1998, # 5, p. 1249 - 1256
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 23, p. 10735 - 10741
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 5738 - 5746
[4] Chemische Berichte, 1887, vol. 20, p. 1017
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1834 - 1840
[6] Synlett, 2001, # 1, p. 93 - 95
[7] Patent: CN107082769, 2017, A, . Location in patent: Paragraph 0017; 0018
  • 4
  • [ 6968-28-1 ]
  • [ 171011-37-3 ]
YieldReaction ConditionsOperation in experiment
100% With borane-THF In tetrahydrofuran at 0 - 20℃; for 3 h; To a solution of 4-bromophthalic acid (3.0 g, 12.24 [MMOL)] in 30 mL of THF was added a solution of borane-THF complex (1. OM) dropwise at 0 [°C.] The solution was warmed to rt and stirred for 3 h. The reaction mixture was quenched by addition of HCI (2N) at 0 [°C.] The product was extracted with ethyl acetate and washed with sat. [NACI,] dried over [NA2SC4,] and concentrated under reduced pressure to afford 2.8 g (100percent) of 4-bromo-2- hydroxymethylbenzyl alcohol as a [COLORLESS OIL.APOS;H] NMR [(CDCK)] 7.28 (m, 2 H), 7.26 (m, 1 H), 4.69 (s, 4 H), 2.80 (bs, [2 H).] To a solution of oxalyl chloride (2.37 mL, 4.607 mmol) in DCM (20 mL) was added dropwise DMSO (1.95 mL) [AT-78 °C.] The mixture was stirred at-78 °C for 30 min and a solution of the diol (1.00 g, 4.607 [MMOL)] was added dropwise. The reaction mixture was stirred for 2 hr and TEA (11.5 mL) was added. The reaction mixture was warmed to rt and water was added. The organic layer was separated and washed with sat. NaCl, dried over Na2SO4, and concentrated under reduced pressure to give [4-BROMO-BENZENE-1,] 2- dicarbaldehyde as a yellow oil (0.450 g, 46percent). A mixture of [4-BROMO-BENZENE-1,] [2-DICARBALDEHYDE] (0.450 g, 2.137 mmol), diethylamino malonate (0.452 g, 2.137 mmol), and sodium ethoxide (0.218 g, 3.20 [MMOL)] in anhydrous ethanol (15 mL) was refluxed for 4 hr. The solution was cooled to rt and concentrated under reduced pressure. The crude residue was purified by flash column chromatography (silica gel, 0. 5percent MeOH in [CHCI3)] to obtain 0.460 g (78percent) of the [7-BROMO-] isoquinoline-3-carboxylic acid ethyl ester which was [HYDROLYZED] according to general procedure C yielding the 0.350 g (85percent) of 7-bromo-isoquinoline-3-carboxylic acid as a white solid. LC/MS [(M/Z)] : 253 (M+1) [+.] [(2S)-AMINO-3-BIPHENYL-4YL-PROPIONIC] acid methyl ester (340 mg, 13.9 [MMOL)] was reacted with 7-bromo-isoquinoline-3-carboxylic acid (350 mg, 13.9 [MMOL)] as described in general procedure A. The resulting compound was hydrolyzed by following general procedure C yielding the title compound (132 mg, 81 percent) as a white solid
79% With dimethylsulfide borane complex In tetrahydrofuran at -10 - 55℃; for 15 h; Inert atmosphere To a solution of acid or diacid (1.0 equiv) in anhydrous THF (4.3 mL per mmol of acid or diacid) at -10 °C under a nitrogen atmosphere was added dropwise a solution of BH3.DMS(1.5-3.0 equiv) in anhydrous THF (0.1 mL per mmol of acid or diacid). The reaction was maintained at -10 °C for 10 min before being heated to 55 °C for 12-16 h. After cooling to rt, an aqueous solution of NaOH (2 M, 4.4 mL per mmol of acid or diacid) was added dropwise and the solution was stirred at rt for 50 min. The organics were extracted with EtOAc, combined, washed with brine, driedover MgSO4 and concentrated in vacuo to afford the desired diol.
75.9% With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; To a stirred solution of 4-bromophthalic acid (9.0 g, 37.55 mmol, 1 equiv) in THF (90 mL) was added drop wise BH3.DMS (35 mL, 375 mmol, 10 equiv) at 0°C. The reaction mixture was warmed to room temperature and stirred for overnight. The reaction mixture was cooled and quenched with MeOH slowly then evaporated to obtain crude product which was purified by silica gel flash column chromatography. The compound eluted out in 1 .5percent MeOH:DCM. The fractions with product were evaporated to obtain (4-bromo-1 ,2- phenylene)dimethanol as white solid (6.0 g, 75.9percent). (0710) 1H NMR (400 MHz, DMSO-de) δ ppm 4.45 (d, J=5.2 Hz, 2H), 4.51 (d, J=5.2 Hz, 2H), 5.12 (t, J=5.6 Hz, 1 H), 5.20 (t, J=1 1 .4 Hz, 1 H), 7.31 (d, J=8.0 Hz, 1 H), 7.40 (t, J=8.0 Hz, 1 H), 7.54 (s, 1 H).
Reference: [1] Patent: WO2004/14844, 2004, A2, . Location in patent: Page 185-186
[2] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 381 - 393
[3] Tetrahedron, 2018, vol. 74, # 2, p. 224 - 239
[4] Patent: WO2018/15879, 2018, A1, . Location in patent: Page/Page column 84
[5] Patent: US2006/35897, 2006, A1, . Location in patent: Page/Page column 22
[6] Patent: WO2008/8821, 2008, A2, . Location in patent: Page/Page column 41
[7] Patent: US2009/298894, 2009, A1, . Location in patent: Page/Page column 49
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  • [ 87639-57-4 ]
Reference: [1] Patent: US5968908, 1999, A,
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  • [ 67-56-1 ]
  • [ 6968-28-1 ]
  • [ 87639-57-4 ]
Reference: [1] Journal of the American Chemical Society, 2018,
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  • [ 70484-01-4 ]
Reference: [1] Helvetica Chimica Acta, 2004, vol. 87, # 4, p. 825 - 844
  • 8
  • [ 6968-28-1 ]
  • [ 660830-63-7 ]
Reference: [1] Patent: WO2018/15879, 2018, A1,
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  • [ 660830-62-6 ]
Reference: [1] Patent: WO2018/15879, 2018, A1,
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