Bromine → HCID 68537594, compound

HRID 1992976Notes

Reaction equation

HRID 1992976 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH:7]([CH2:14][CH2:15][CH3:16])[CH2:6]2.[Br:17]Br>C(Cl)(Cl)Cl>[Br:17][C:8]1[C:7]([CH2:14][CH2:15][CH3:16])=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]=1[OH:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 68537219HCID 68537219, compound

Product 1

HCID 68537594HCID 68537594, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 6-Methoxy-3-propyl-3,4-dihydro-2H-naphthalen-1-one (93) (1.6 g, 7.33 mmol) in dry chloroform (65 mL) was added dropwise via an addition funnel bromine (2.35 g, 14.7 mmol) in chloroform (20 mL). The reaction mixture was stirred at ambient temperature for 20 h. The reaction mixture was concentrated to afford the title compound as oil, 2.76 g. The crude material (2.76 g, 7.33 mmol) in dry acetonitrile (64 mL) was cooled to −10° C., 1,8-diazabicyclo[5.4.0]undec-7-ene (1.64 mL, 10.99 mmol) in dry acetonitrile (8 mL) was added dropwise via an addition funnel. The reaction mixture was quenched with 1 N HCl (50 mL) after stirring for 1 h at 6° C. The aqueous layer was extracted with EtOAc, the organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified with 1:9 EtOAc:hexanes over 40 min to obtain 1.41 g (65%) of the title compound (94). 1H NMR (400 MHz, d-CDCl3): δ 1.01 (t, J=7.3 Hz, 3H), 1.68-1.74 (m, 2H), 2.79 (t, J=7.7 Hz, 2H), 3.90 (s, 3H), 6.06 (s, 1H), 7.00-7.01 (m, 1H), 7.08 (dd, J1=2.6 Hz, J2=9.1 Hz, 1H), 7.17 (s, 1H), 8.07 (d, J=9.1 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-25145b83816e4f5c9cc7c7b210bf4d42
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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