Bromine → HCID 86714054, compound

HRID 576345Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)=[CH:6][C:5]([C@H:18]2[C@H:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[O:19]2)=[CH:4][C:3]=1[OH:57].[Br:58]Br.[Cl-].[NH4+]>CC(O)=O>[Br:58][C:4]1[C:5]([C@H:18]2[C@H:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[O:19]2)=[CH:6][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)=[C:2]([Cl:1])[C:3]=1[OH:57]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of compound 77 (2.36 g, 3.0 mmol) in AcOH (30 mL) were added TEA (0.6 mL, 4.51 mmol) and Br2 (0.18 mL, 3.61 mmol) dropwise at 0° C. The mixture was stirred at 0° C. for 15 min and at room temperature for 15 hours. To a mixture was added saturated ammonium chloride and extracted with EtOAc (100 mL). The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was carried on to the next step without purification.

Workup

extractionextracted with EtOAc (100 mL)
washThe organic layer was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was carried on to the next step without purification

Sources & evidence

ORD record: ord-d895943c827941e98e45245cb6ed2702
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034921B2

Reaction notes

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