Water → HCID 66879234, compound

HRID 2265888Notes

Reaction equation

HRID 2265888 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25]C)(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br.O>ClCCl>[F:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[OH:25])(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 66879518HCID 66879518, compound

Product 1

HCID 66879234HCID 66879234, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

620 mg (1.54 mmol) of 4-(4-fluorophenoxy)-N-[2-(2-methoxyphenyl)ethyl]benzene-sulfonamide are dissolved in 10 ml of dichloromethane and, at −40° C., 3.09 ml (3.09 mmol) of a 1 M solution of boron tribromide in dichloromethane are added. The solution is warmed to room temperature and stirred for a further four hours. It is subsequently added to water, the phases are separated, and the organic phase is washed twice more with H2O. The dichloromethane phase is dried with MgSO4 and concentrated, allowing the desired phenol to be isolated as a brown oil. Crude yield 89%.

Workup

  1. customthe phases are separated
  2. washthe organic phase is washed twice more with H2O
  3. dry with materialThe dichloromethane phase is dried with MgSO4
  4. concentrationconcentrated
  5. customto be isolated as a brown oil

Sources & evidence

ORD record
ord-bd7d4d5013464bef9b121b3e7369f436
Source dataset
uspto-grants-2010_12
Patent number
US07858619B2

Reaction notes

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