Boron tribromide dichloromethane → HCID 68862270, compound

HRID 898887Notes

Reaction equation

HRID 898887 reaction equation
[F:1][C:2]([F:29])([F:28])[O:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:27])[N:12]([CH2:25][CH3:26])[CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23]C)[CH:19]=3)[CH2:14]2)=[CH:6][CH:5]=1.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[F:1][C:2]([F:28])([F:29])[O:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11](=[O:27])[N:12]([CH2:25][CH3:26])[CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([OH:23])[CH:19]=3)[CH2:14]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 68862803HCID 68862803, compound

Product 1

HCID 68862270HCID 68862270, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl-(6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid 4-trifluoromethoxy-phenyl ester (898.6 mg; 2.19 mmol) in anhydrous CH2Cl2 (8 mL) was cooled to −78° C., a 1.0 M solution of boron tribromide-CH2Cl2 (6.57 mL, 6.57 mmol) was added slowly. Upon completion of the addition, the reaction mixture was allowed to warm to RT, quenched with MeOH (10 mL) and stirred for an additional 2 h. The solvents were evaporated, and the residue was purified by flash chromatography with hexane-EtOAc (2.5:1) to give 649.4 mg (75%) of ethyl-(6-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid 4-trifluoromethoxy-phenyl ester as a white solid.

Workup

  1. additionUpon completion of the addition
  2. customquenched with MeOH (10 mL)
  3. customThe solvents were evaporated
  4. customthe residue was purified by flash chromatography with hexane-EtOAc (2.5:1)

Sources & evidence

ORD record
ord-92a0c7d9c2124170993b2272f45b9564
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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