tert-Butanol → Tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoate

HRID 1778364Notes

Reaction equation

HRID 1778364 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:21]1([S:27]([CH2:30][C:31]2[C:36]([C:37](O)=[O:38])=[C:35]([OH:40])[C:34]([Br:41])=[CH:33][CH:32]=2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C1C=CN=CC=1)C.C1COCC1>[C:21]1([S:27]([CH2:30][C:31]2[C:36]([C:37]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:38])=[C:35]([OH:40])[C:34]([Br:41])=[CH:33][CH:32]=2)(=[O:29])=[O:28])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 666850906-(Benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoic acid2×

Product 1

HCID 66686379Tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butanol (1 mL) and N,N′-dicyclohexylcarbodiimide (0.4 g) were added to a solution of 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoic acid (Intermediate 39, 0.48 g) and DMAP (0.016 g) in THF (10 mL) and the mixture was stirred for 18 hours. It was evaporated to dryness and the residue was suspended in DCM and the insoluble material was removed by filtration. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with DCM to give tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoate (0.34 g).

Workup

  1. customIt was evaporated to dryness
  2. customthe insoluble material was removed by filtration
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was purified by chromatography on silica
  5. washeluting with DCM

Sources & evidence

ORD record
ord-b8da9eff06844eb9b52fc214fc196707
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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