Hydrochloric Acid → HCID 18415111, compound

HRID 991978Notes

Reaction equation

HRID 991978 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:22])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH:19]([CH3:21])[CH3:20])[CH:13]=1)[C:5](O)=[O:6].B([O-])[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C(Br)C.Cl>C(Cl)Cl.O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:22])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH:19]([CH3:20])[CH3:21])[CH:13]=1)[CH2:5][OH:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 9932398HCID 9932398, compoundHCID 178449041HCID 178449041, compound

Product 1

HCID 18415111HCID 18415111, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)benzoic acid (Example 1(c) (1.0 g, 3.3 mmol), tetrabutylammonium boronate (2.6 g, 9.9 mmol) and ethylbromide (1.0 ml, 13.2 mmol) in 25 ml of CH2Cl2 and 10 ml of tetrahydrofuran was stirred at room temperature over night. The reaction mixture was treated with 1M HCl and extracted several times with EtOAc. The combined organic phases were washed once with water followed by a saturated solution of NaCl. After drying over MgSO4, filtration and evaporation, the residue was purified by column chromathography (silica gel, 7:3 p-ether/EtOAc). This gave 0.922 g (98%) of 3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy) benzyl-alcohol.

Workup

  1. extractionextracted several times with EtOAc
  2. washThe combined organic phases were washed once with water
  3. dry with materialAfter drying over MgSO4, filtration and evaporation
  4. customthe residue was purified by column chromathography (silica gel, 7:3 p-ether/EtOAc)

Sources & evidence

ORD record
ord-fdab3f2131fd47e7bec390ade8516305
Source dataset
uspto-grants-2002_10
Patent number
US06465687B1

Reaction notes

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