Boron tribromide → N-[4-chloro-3-(trifluoromethyl)phenyl]-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide

HRID 1640166Notes

Reaction equation

HRID 1640166 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][C:15]([O:21]C)=[CH:16][CH:17]=3)[CH2:12]2)=[O:10])=[CH:4][C:3]=1[C:23]([F:26])([F:25])[F:24].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][C:15]([OH:21])=[CH:16][CH:17]=3)[CH2:12]2)=[O:10])=[CH:4][C:3]=1[C:23]([F:24])([F:25])[F:26]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58902339N-[4-chloro-3-(trifluoromethyl)phenyl]-7-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide

Product 1

HCID 58902317N-[4-chloro-3-(trifluoromethyl)phenyl]-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxamideYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-[4-chloro-3-(trifluoromethyl)phenyl]-7-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide (3.65 g mg, 9.53 mmol) in DCM (100 mL) at 0° C. was added a 1.0M solution of BBr3 in DCM (14.3 mL) dropwise. The reaction mixture was allowed to warm to rt overnight. The reaction mixture was poured onto ice and extracted with EtOAc. The organic solution was dried over Na2SO4, filtered and evaporated. The residue was triturated with DCM to give N-[4-chloro-3-(trifluoromethyl)phenyl]-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide as a beige solid (3.25 g, 92.4%). LCMS: (FA) ES+ 370.2, ES− 368.1.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionextracted with EtOAc
  3. dry with materialThe organic solution was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was triturated with DCM

Sources & evidence

ORD record
ord-488d77c39a31452b9db4a71c72d0fa95
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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