Hydrochloric Acid → 9-Bromo-8-fluoro-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylic acid

HRID 575023Notes

Reaction equation

HRID 575023 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]2[CH:9](CC)[CH2:10][O:11][C:12]3[CH:19]=[C:18]([F:20])[C:17]([Br:21])=[CH:16][C:13]=3[C:14]=2[N:15]=1)=[O:5])C.O1CCCC1.[Li+].[OH-].Cl>O>[Br:21][C:17]1[C:18]([F:20])=[CH:19][C:12]2[O:11][CH2:10][CH2:9][C:8]3[S:7][C:6]([C:4]([OH:5])=[O:3])=[N:15][C:14]=3[C:13]=2[CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86693058ethyl 9-Bromo-8-fluoro-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid ethyl ester

Product 1

HCID 866930579-Bromo-8-fluoro-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylic acidYield 80.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 10-L 4-necked round-bottom flask purged and maintained with an inert atmosphere of argon was placed ethyl 9-Bromo-8-fluoro-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid ethyl ester (350 g, 940.33 mmol, 1.00 equiv), tetrahydrofuran (1.3 L), water (2.6 L), and LiOH (62 g, 2.59 mol, 2.73 equiv). The resulting solution was stirred at room temperature for 3 h, cooled to <10° C. and adjusted to pH=2-3 with hydrochloric acid. The precipitates were collected by filtration, washed with 4×1 L of water and dried to afford 260 g (80%) of 9-Bromo-8-fluoro-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid as a brown solid.

Workup

  1. customInto a 10-L 4-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of argon
  3. temperaturecooled to <10° C.
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with 4×1 L of water
  6. customdried

Sources & evidence

ORD record
ord-11fad1ec2a374413a72fd5310aa9cd7a
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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