Water → 3,3-Dimethyl-2,3-dihydro-1-benzofuran-4-ol

HRID 527543Notes

Reaction equation

HRID 527543 reaction equation
[CH3:1][C:2]1([CH3:13])[C:6]2[C:7]([O:11]C)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.B(Br)(Br)Br.O>ClCCl>[CH3:1][C:2]1([CH3:13])[C:6]2=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=[C:5]2[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 575170913,3-Dimethyl-4-(methyloxy)-2,3-dihydro-1-benzofuran2×

Product 1

HCID 574112993,3-Dimethyl-2,3-dihydro-1-benzofuran-4-olYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,3-dimethyl-4-(methyloxy)-2,3-dihydro-1-benzofuran (Intermediate 49, 4.0 g) in dichloromethane (100 ml, SCRC) was added BBr3 (6.37 ml, 67.3 mmol, SCRC) dropwise under ice-cooling. After the addition was complete, the reaction mixture was stirred for 2 hours at room temperature and then water (20 ml) was added. The resulting mixture was extracted with ethyl acetate (3 times 100 ml, SCRC) and the combined organic layers were dried, evaporated and purified by silica gel chromatography with EtOAc/PE as eluents (1/20) to afford the title compound (2.8 g).

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. extractionThe resulting mixture was extracted with ethyl acetate (3 times 100 ml, SCRC)
  4. customthe combined organic layers were dried
  5. customevaporated
  6. custompurified by silica gel chromatography with EtOAc/PE as eluents (1/20)

Sources & evidence

ORD record
ord-98dba7ad6b4a46b78903b64a4c9cc28e
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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